Please use this identifier to cite or link to this item: https://doi.org/10.1002/adsc.201100227
Title: Synthesis of sulfur-substituted α-stereogenic amides and ketones: Highly enantioselective sulfa-michael additions of 1,4-dicarbonylbut-2-enes
Authors: Zhao, F.
Zhang, W.
Yang, Y.
Pan, Y.
Chen, W.
Liu, H.
Yan, L.
Tan, C.-H. 
Jiang, Z.
Keywords: α-stereogenic amides and ketones
1,4-dicarbonylbut-2-enes
asymmetric catalysis
organocatalysis
sulfa-Michael addition
Issue Date: Oct-2011
Citation: Zhao, F., Zhang, W., Yang, Y., Pan, Y., Chen, W., Liu, H., Yan, L., Tan, C.-H., Jiang, Z. (2011-10). Synthesis of sulfur-substituted α-stereogenic amides and ketones: Highly enantioselective sulfa-michael additions of 1,4-dicarbonylbut-2-enes. Advanced Synthesis and Catalysis 353 (14-15) : 2624-2630. ScholarBank@NUS Repository. https://doi.org/10.1002/adsc.201100227
Abstract: Conjugate addition to 1,4-dicarbonylbut-2-enes will generate an α-stereogenic center with respect to one of the carbonyl groups, which informally, can be considered as an inversion of normal reactivity patterns or umpolung protocol. In this paper, the addition of tert-butyl mercaptan to 1,4-dicarbonylbut-2-enes including (E)-4-oxo-4-arylbutenamides and (E)-4-oxo-4-arylbutenones has been developed, to synthesize a series of chiral sulfur-substituted α-stereogenic amides and ketones in high regioselectivity and enantioselectivity (up to 98% ee). Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Source Title: Advanced Synthesis and Catalysis
URI: http://scholarbank.nus.edu.sg/handle/10635/77188
ISSN: 16154150
DOI: 10.1002/adsc.201100227
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