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Enantioselective nickel-catalyzed arylative intramolecular 1,4allylations (2018)
Journal Article
Nguyen, T. L. N., Incerti-Pradillos, C. A., Lewis, W., & Lam, H. W. (in press). Enantioselective nickel-catalyzed arylative intramolecular 1,4allylations. Chemical Communications, https://doi.org/10.1039/C8CC03204A

The enantioselective nickel-catalyzed desymmetrization of allenyl cyclohexa-2,5-dienones by reaction with arylboronic acids is described. Nickel-catalyzed arylation of the allene gives allylnickel species, which undergo cyclization by 1,4allylation t... Read More about Enantioselective nickel-catalyzed arylative intramolecular 1,4allylations.

Switchable Synthesis of Z-Homoallylic Boronates and E-Allylic Boronates by Enantioselective Copper-Catalyzed 1,6-Boration (2018)
Journal Article
Luo, Y., Wales, S. M., Korkis, S. E., Roy, I. D., Lewis, W., & Lam, H. W. (2018). Switchable Synthesis of Z-Homoallylic Boronates and E-Allylic Boronates by Enantioselective Copper-Catalyzed 1,6-Boration. Chemistry - A European Journal, 24(33), 8315-8319. https://doi.org/10.1002/chem.201801804

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim The enantioselective Cu-catalyzed 1,6-boration of (E,E)-α,β,γ,δ-unsaturated ketones is described, which gives homoallylic boronates with high enantiomeric purity and unexpectedly high Z-selectivity.... Read More about Switchable Synthesis of Z-Homoallylic Boronates and E-Allylic Boronates by Enantioselective Copper-Catalyzed 1,6-Boration.

One-carbon oxidative annulations of 1,3-enynes by catalytic C–H functionalization and 1,4-rhodium(III) migration (2018)
Journal Article
Dooley, J. D., & Lam, H. W. (2018). One-carbon oxidative annulations of 1,3-enynes by catalytic C–H functionalization and 1,4-rhodium(III) migration. Chemistry - A European Journal, 24(16), 4050-4054. https://doi.org/10.1002/chem.201706043

Rhodium(III)-catalyzed C-H functionalization-oxidative annulations of aromatic substrates with 1,3-enynes that contain allylic hydrogen atoms cis to the alkyne are described. The key step in these reactions is an alkenyl-to-allyl 1,4-rhodium(III) mig... Read More about One-carbon oxidative annulations of 1,3-enynes by catalytic C–H functionalization and 1,4-rhodium(III) migration.

Enantioselective rhodium-catalyzed coupling of arylboronic acids, 1,3-enynes, and Imines by alkenyl-to-allyl 1,4-rhodium(I) migration (2017)
Journal Article
Callingham, M., Partridge, B. M., Lewis, W., & Lam, H. W. (2017). Enantioselective rhodium-catalyzed coupling of arylboronic acids, 1,3-enynes, and Imines by alkenyl-to-allyl 1,4-rhodium(I) migration. Angewandte Chemie International Edition, 56(51), https://doi.org/10.1002/anie.201709334

A chiral rhodium complex catalyzes the highly enantioselective coupling of arylboronic acids, 1,3-enynes, and imines to give homoallylic sulfamates. The key step is the generation of allylrhodium(I) species by alkenyl-to-allyl 1,4-rhodium(I) migratio... Read More about Enantioselective rhodium-catalyzed coupling of arylboronic acids, 1,3-enynes, and Imines by alkenyl-to-allyl 1,4-rhodium(I) migration.

Sulfonylative and azidosulfonylative cyclizations by visible-light-photosensitization of sulfonyl azides in THF (2017)
Journal Article
Zhu, S., Pathigoolla, A., Lowe, G., Walsh, D. A., Cooper, M., Lewis, W., & Lam, H. W. (2017). Sulfonylative and azidosulfonylative cyclizations by visible-light-photosensitization of sulfonyl azides in THF. Chemistry - A European Journal, 23(69), https://doi.org/10.1002/chem.201704380

The generation of sulfonyl radicals from sulfonyl azides using visible light and a photoactive iridium complex in THF is described. This process was used to promote sulfonylative and azidosulfonylative cyclizations of enynes to give several classes o... Read More about Sulfonylative and azidosulfonylative cyclizations by visible-light-photosensitization of sulfonyl azides in THF.

Enantioselective nickel-catalyzed intramolecular allylic alkenylations enabled by reversible alkenylnickel E/Z isomerization (2017)
Journal Article
Yap, C., Lenagh-Snow, G. M., Narayan Karad, S., Lewis, W., Diorazio, L. J., & Lam, H. W. (in press). Enantioselective nickel-catalyzed intramolecular allylic alkenylations enabled by reversible alkenylnickel E/Z isomerization. Angewandte Chemie International Edition, 56, https://doi.org/10.1002/anie.201703380

Enantioselective nickel-catalyzed arylative cyclizations of substrates containing a Z-allylic phosphate tethered to an alkyne are described. These reactions give multisubstituted chiral aza- and carbocycles, and are initiated by the addition of an ar... Read More about Enantioselective nickel-catalyzed intramolecular allylic alkenylations enabled by reversible alkenylnickel E/Z isomerization.

Arylative intramolecular allylation of ketones with 1,3-enynes enabled by catalytic alkenyl-to-allyl 1,4-Rh(I) migration (2017)
Journal Article
Partridge, B. . M., Callingham, M., Lewis, W., & Lam, H. W. (2017). Arylative intramolecular allylation of ketones with 1,3-enynes enabled by catalytic alkenyl-to-allyl 1,4-Rh(I) migration. Angewandte Chemie International Edition, 56(25), https://doi.org/10.1002/anie.201703155

Alkenyl-to-allyl 1,4-Rh(I) migration enables the generation of nucleophilic allylrhodium(I) species by remote C–H activation. This new mode of reactivity was employed in the diastereoselective reaction of arylboron reagents with substrates containing... Read More about Arylative intramolecular allylation of ketones with 1,3-enynes enabled by catalytic alkenyl-to-allyl 1,4-Rh(I) migration.

Rhodium-catalyzed oxidative C–H allylation of benzamides with 1,3-dienes by allyl-to-allyl 1,4-Rh(III) migration (2016)
Journal Article
Korkis, S. E., Burns, D. J., & Lam, H. W. (in press). Rhodium-catalyzed oxidative C–H allylation of benzamides with 1,3-dienes by allyl-to-allyl 1,4-Rh(III) migration. Journal of the American Chemical Society, https://doi.org/10.1021/jacs.6b06884

The Rh(III)-catalyzed oxidative C–H allylation of N-acetylbenzamides with 1,3-dienes is described. The presence of allylic hydrogens cis- to the less substituted alkene of the 1,3-diene is important for the success of these reactions. With the assist... Read More about Rhodium-catalyzed oxidative C–H allylation of benzamides with 1,3-dienes by allyl-to-allyl 1,4-Rh(III) migration.

Enantioselective nickel-catalyzed anti-carbometallative cyclizations of alkynyl electrophiles enabled by reversible alkenylnickel E/Z isomerization (2016)
Journal Article
Clarke, C., Incerti-Pradillos, C. A., & Lam, H. W. (2016). Enantioselective nickel-catalyzed anti-carbometallative cyclizations of alkynyl electrophiles enabled by reversible alkenylnickel E/Z isomerization. Journal of the American Chemical Society, 138(26), https://doi.org/10.1021/jacs.6b04206

Nickel-catalyzed additions of arylboronic acids to alkynes, followed by enantioselective cyclizations of the alkenylnickel species onto tethered ketones or enones, are reported. These reactions are reliant upon the formal anti-carbonickelation of the... Read More about Enantioselective nickel-catalyzed anti-carbometallative cyclizations of alkynyl electrophiles enabled by reversible alkenylnickel E/Z isomerization.

Copper-catalyzed borylative coupling of vinylazaarenes and N-Boc imines (2016)
Journal Article
Smith, J. J., Best, D., & Lam, H. W. (2016). Copper-catalyzed borylative coupling of vinylazaarenes and N-Boc imines. Chemical Communications, https://doi.org/10.1039/C6CC00603E

Cu-catalyzed three-component couplings of vinylazaarenes, B2(pin)2, and N-Boc imines are described. Oxidation of the initially formed boronate gives azaarene-containing, Boc-protected amino alcohols with reasonable to good diastereoselectivities.

Chain walking of allylrhodium species towards esters during rhodium-catalyzed nucleophilic allylations of imines (2015)
Journal Article
Martínez, J. I., Smith, J. S., Hepburn, H. B., & Lam, H. W. (2016). Chain walking of allylrhodium species towards esters during rhodium-catalyzed nucleophilic allylations of imines. Angewandte Chemie International Edition, 55(3), 1108-1112. https://doi.org/10.1002/anie.201508964

Allylrhodium species derived from ?-trifluoroboryl ?,?-unsaturated esters undergo chain walking towards the ester moiety.The resulting allylrhodium species react with imines to give products containing two new stereocenters and a Z-alkene. By using a... Read More about Chain walking of allylrhodium species towards esters during rhodium-catalyzed nucleophilic allylations of imines.

Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C—H Functionalization and Spiroannulation (2015)
Journal Article
Reddy Chidipudi, S., Burns, D. J., Khan, I., & Lam, H. W. (2015). Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C—H Functionalization and Spiroannulation. Angewandte Chemie International Edition, 54(47), 13975-13979. https://doi.org/10.1002/anie.201507029

Chiral cyclopentadienyl rhodium complexes promote highly enantioselective enol?directed C(sp2)?H functionalization and oxidative annulation with alkynes to give spiroindenes containing all?carbon quaternary stereocenters. High selectivity between two... Read More about Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C—H Functionalization and Spiroannulation.

Direct Synthesis of 5-Aryl Barbituric Acids by Rhodium(II)-Catalyzed Reactions of Arenes with Diazo Compounds (2015)
Journal Article
Best, D., Burns, D. J., & Lam, H. W. (2015). Direct Synthesis of 5-Aryl Barbituric Acids by Rhodium(II)-Catalyzed Reactions of Arenes with Diazo Compounds. Angewandte Chemie International Edition, 54(25), 7410-7413. https://doi.org/10.1002/anie.201502324

A commercially available rhodium(II) complex catalyzes the direct arylation of 5?diazobarbituric acids with arenes, allowing straightforward access to 5?aryl barbituric acids. Free N--H groups are tolerated on the barbituric acid, with no complicatio... Read More about Direct Synthesis of 5-Aryl Barbituric Acids by Rhodium(II)-Catalyzed Reactions of Arenes with Diazo Compounds.

Enantioselective copper-catalyzed reductive coupling of vinylazaarenes with N-Boc aldimines (2015)
Journal Article
Choi, B., Saxena, A., Smith, J. J., Churchill, G. H., & Lam, H. W. (2015). Enantioselective copper-catalyzed reductive coupling of vinylazaarenes with N-Boc aldimines. SYNLETT, 26(3), https://doi.org/10.1055/s-0034-1379548

The diastereo- and enantioselective reductive coupling of vinylazaarenes with N-Boc aldimines is described. The reactions proceed using chiral copper–bisphosphine complexes in the presence of TMDS as a hydride source to give reductive coupling produc... Read More about Enantioselective copper-catalyzed reductive coupling of vinylazaarenes with N-Boc aldimines.

Synthesis of spiroindanes by palladium-catalyzed oxidative annulations of non- or weakly activated 1,3-dienes involving C–H functionalization (2015)
Journal Article
Khan, I., Chidipudi, S. R., & Lam, H. W. (2015). Synthesis of spiroindanes by palladium-catalyzed oxidative annulations of non- or weakly activated 1,3-dienes involving C–H functionalization. Chemical Communications, 51, https://doi.org/10.1039/C4CC09496D

The synthesis of spiroindanes by the palladium-catalyzed oxidative annulation of non- or weakly activated 1,3-dienes with 2-aryl cyclic 1,3-dicarbonyl compounds is described. Examples of the dearomatizing oxidative annulation of 1,3-dienes with 1-ary... Read More about Synthesis of spiroindanes by palladium-catalyzed oxidative annulations of non- or weakly activated 1,3-dienes involving C–H functionalization.

Catalytic 1,4-rhodium(III) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in C-H functionalizations (2014)
Journal Article
Burns, D. J., & Lam, H. W. (2014). Catalytic 1,4-rhodium(III) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in C-H functionalizations. Angewandte Chemie International Edition, 53(37), https://doi.org/10.1002/anie.201406072

1,3?Enynes containing allylic hydrogens cis to the alkyne are shown to act as one?carbon partners, rather than two?carbon partners, in various rhodium?catalyzed oxidative annulations. The mechanism of these unexpected transformations is proposed to o... Read More about Catalytic 1,4-rhodium(III) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in C-H functionalizations.