Organocatalytic Enantioselective Cascade Michael−Michael−Wittig Reactions of Phosphorus Ylides: One-Pot Synthesis of the all-cis Trisubstituted Cyclohexenecarboxylates via the [1 + 2 + 3] Annulation | Zendy

BorCherng Hong | Zendy; Rei-Hau Jan | Zendy; ChihWei Tsai | Zendy; Roshan Y. Nimje | Zendy; JuHsiou Liao | Zendy; GeneHsiang Lee | Zendy

Open Access

Organocatalytic Enantioselective Cascade Michael−Michael−Wittig Reactions of Phosphorus Ylides: One-Pot Synthesis of the all-cis Trisubstituted Cyclohexenecarboxylates via the [1 + 2 + 3] Annulation

Author(s) -

BorCherng Hong,

Rei-Hau Jan,

ChihWei Tsai,

Roshan Y. Nimje,

JuHsiou Liao,

GeneHsiang Lee

Publication year - 2009

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol9021832

Subject(s) - michael reaction , chemistry , annulation , enantioselective synthesis , wittig reaction , stereoselectivity , cascade , organocatalysis , phosphorus , organic chemistry , nitro , catalysis , stereochemistry , alkyl , chromatography

The stereoselective synthesis of all-cis 5-nitro-4,6-diphenylcyclohex-1-enecarboxylic ester has been achieved by an organocatalytic asymmetric Michael-Michael-Wittig cascade reaction of phosphorus ylides, nitroolefins, and alpha,beta-unsaturated aldehydes with excellent enantioselectivities (up to >99% ee).

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