In:
Angewandte Chemie, Wiley, Vol. 128, No. 44 ( 2016-10-24), p. 14063-14066
Abstract:
A general and practical Pd II ‐catalyzed intermolecular silylation of primary and secondary C−H bonds of α‐amino acids and simple aliphatic acids is reported. This method provides divergent and stereoselective access to a variety of optical pure β‐silyl‐α‐amino acids, which are useful for genetic technologies and proteomics. It can also be readily performed on a gram scale and the auxiliary can be easily removed with retention of configuration. The synthetic importance of this method is further demonstrated by the late‐stage functionalization of biological small molecules, such as (−)‐santonin and β‐cholic acid. Moreover, several key palladacycles were successfully isolated and characterized to elucidate the mechanism of this β−C(sp 3 )‐H silylation process.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v128.44
DOI:
10.1002/ange.201607766
Language:
English
Publisher:
Wiley
Publication Date:
2016
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