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1,3‐Dipolar Cycloadditions of Carbonyl Ylides to Aldimines: Scope, Limitations and Asymmetric Cycloadditions
Author(s) -
Torssell Staffan,
Somfai Peter
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600324
Subject(s) - chemistry , enantioselective synthesis , aldimine , cycloaddition , enantiomer , 1,3 dipolar cycloaddition , catalysis , enantiomeric excess , organic chemistry , stereochemistry , combinatorial chemistry
The development of a diastereoselective 1,3‐dipolar cycloaddition of carbonyl ylides and imines for the synthesis of α‐hydroxy‐β‐amino esters is described. The methodology is successfully applied to chiral α‐methylbenzylimines affording enantiomerically pure syn ‐β‐amino alcohols, which is exemplified with a short asymmetric synthesis of the paclitaxel side‐chain. The use of chiral Rh(II) carboxylate catalysts for the development of a catalytic enantioselective 1,3‐dipolar cycloaddition is also described, affording syn ‐β‐amino alcohols in modest enantiomeric purity ( e.r. up to 82:18).