Highly Enantioselective Aza-Baylis-Hillman-Type Reaction of α,β-Unsaturated Aldehydes with In Situ Generated N-Boc- and N-Cbz-Imines

An organocatalytic highly enantioselective aza‐Baylis–Hillman reaction of α,β‐unsaturated aldehydes with in situ generated N‐Boc‐ and N‐Cbz‐imines is presented. This novel process opens the pathway for the synthesis of β‐amino carbonyl compounds bearing an α‐alkylidene group under mild and simple co...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2009-12, Vol.2009 (36), p.6277-6280
Main Authors: CIHALOVA, Sylva, REMES, Marek, CISAROVA, Ivana, VESELY, Jan
Format: Article
Language:English
Subjects:
Aza-Baylis-Hillman reaction
Catalysis
Catalytic reactions
Chemistry
Dia­stereoselectivity
Enantioselectivity
Exact sciences and technology
General and physical chemistry
Noncondensed benzenic compounds
Organic chemistry
Organocatalysis
Preparations and properties
Sulfur
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:An organocatalytic highly enantioselective aza‐Baylis–Hillman reaction of α,β‐unsaturated aldehydes with in situ generated N‐Boc‐ and N‐Cbz‐imines is presented. This novel process opens the pathway for the synthesis of β‐amino carbonyl compounds bearing an α‐alkylidene group under mild and simple conditions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) Chiral β‐amino carbonyl compounds bearing an α‐alkylidene group were easily synthesized under mild and simple conditions from α,β‐unsaturated aldehydes and α‐amido sulfones in good yields and diastereoselectivities and excellent enantioselectivities.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200900969