Asymmetric synthesis of 3,5-disubstituted indolizidines by intermolecular addition of an allylsilane on an N-acyliminium ion | Zendy

Elisabeth Conchon | Zendy; Yvonne Gelas-Mialhe | Zendy; Roland Remuson | Zendy

Open Access

Asymmetric synthesis of 3,5-disubstituted indolizidines by intermolecular addition of an allylsilane on an N-acyliminium ion

Author(s) -

Elisabeth Conchon,

Yvonne Gelas-Mialhe,

Roland Remuson

Publication year - 2006

Publication title -

tetrahedron asymmetry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.396

H-Index - 107

eISSN - 1362-511X

pISSN - 0957-4166

DOI - 10.1016/j.tetasy.2006.04.027

Subject(s) - indolizidine , enantioselective synthesis , pyroglutamic acid , intermolecular force , chemistry , stereochemistry , ion , organic chemistry , amino acid , catalysis , molecule , alkaloid , biochemistry

A diastereoselective synthesis of 3,5-disubstituted indolizidines based on an intermolecular addition of an allylsilane on an acyliminium ion derived from (S)-pyroglutamic acid is described. The synthetic potential of this methodology is demonstrated by the enantioselective synthesis of (−)-indolizidine 195B, (−)-indolizidine 223AB, (+)-monomorine and (−)-3-butyl-5-propyl indolizidin

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