Enantioselective Cobalt-Catalyzed Intermolecular Hydroacylation of 1,6-Enynes

Angewandte Chemie
Andrew WhyteMark Lautens

Abstract

We report a cobalt-catalyzed hydroacylation of 1,6-enynes with exogenous aldehydes in a domino sequence to construct enantioenriched ketones. The products were obtained in good yields with excellent regio-, diastereo-, and enantioselectivity. Furthermore, the chiral products served as valuable precursors to access complex spirocyclic scaffolds with three contiguous stereocenters. The asymmetric hydroacylation process exhibited no C-H crossover and no KIE, thus indicating that the C-H bond cleavage was not involved in the turnover-limiting step.

References

Nov 17, 2005·Journal of the American Chemical Society·Kousik KunduAndrew T Morehead
Dec 29, 2007·Journal of the American Chemical Society·Wei HeAlison J Frontier
May 7, 2009·Journal of the American Chemical Society·Matthew M CoulterVy M Dong
Oct 31, 2009·Chemical Reviews·Michael C Willis
Oct 27, 2011·Chemistry : a European Journal·Mana IshidaKen Tanaka
Feb 14, 2012·Journal of the American Chemical Society·Adrian B ChaplinMichael C Willis
Mar 1, 2014·Accounts of Chemical Research·Ke Gao, Naohiko Yoshikai
Mar 5, 2014·Journal of the American Chemical Society·Qing-An ChenVy M Dong
Nov 18, 2014·Journal of the American Chemical Society·Junfeng Yang, Naohiko Yoshikai
Dec 17, 2014·Organic Letters·Pin-Sheng Lee, Naohiko Yoshikai
Dec 10, 2015·Journal of the American Chemical Society·Rajagopal SanthoshkumarChien-Hong Cheng
Mar 10, 2016·Journal of the American Chemical Society·Jung-Woo ParkVy M Dong
Oct 21, 2016·Chemistry : a European Journal·Kirsten F JohnsonLevi M Stanley
Apr 30, 2017·Journal of the American Chemical Society·Songjie YuShaozhong Ge
Jul 14, 2017·Journal of the American Chemical Society·Daniel K KimVy M Dong
Nov 10, 2017·Journal of the American Chemical Society·Stanley M JingT V RajanBabu
Aug 17, 2018·Journal of the American Chemical Society·Chao Wang, Shaozhong Ge
Feb 12, 2019·Angewandte Chemie·Zhiwei ChenVy M Dong
Mar 23, 2019·Journal of the American Chemical Society·Kristers OzolsNicolai Cramer
May 12, 2019·Angewandte Chemie·Joachim LoupLutz Ackermann
Sep 3, 2019·Journal of the American Chemical Society·Mahesh M ParsutkarT V RajanBabu
Apr 28, 2020·Journal of the American Chemical Society·Andrew WhyteMark Lautens

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