1,3‐Dipolar Cycloadditions of Carbonyl Ylides to Aldimines: A Three‐Component Approach to  syn ‐α‐Hydroxy‐β‐amino Esters | Zendy

Torssell Staffan | Zendy; Kienle Marcel | Zendy; Somfai Peter | Zendy

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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.

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