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1,3‐Dipolar Cycloadditions of Carbonyl Ylides to Aldimines: A Three‐Component Approach to syn ‐α‐Hydroxy‐β‐amino Esters
Author(s) -
Torssell Staffan,
Kienle Marcel,
Somfai Peter
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200500296
Subject(s) - aldimine , chemistry , enantioselective synthesis , component (thermodynamics) , cycloaddition , amino acid , organic chemistry , side chain , stereochemistry , catalysis , biochemistry , physics , polymer , thermodynamics
A highly diastereoselective Rh II ‐catalyzed 1,3‐dipolar cycloaddition leads to the formation of syn ‐β‐amino alcohols and syn ‐α‐hydroxy‐β‐amino acids in high yields (see scheme; p ‐TSA= para ‐toluenesulfonic acid, Bn=benzyl). This three‐component approach to the addition of metal‐associated carbonyl ylides to aldimines was applied to a short enantioselective synthesis of the C13 side chain of taxol.