Diastereoselective allylation of α-ketoamides bearing camphor N-tosylpyrazolidinone auxiliary:: Efficient synthesis of highly optically active two stereoisomers

被引:16
作者
Chen, JH [1 ]
Venkatesham, U [1 ]
Lee, LC [1 ]
Chen, KM [1 ]
机构
[1] Natl Taiwan Natl Univ, Dept Chem, Taipei 116, Taiwan
关键词
allylation; reversal of stereoselectivity; chiral auxiliary;
D O I
10.1016/j.tet.2005.10.042
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Complementary allylation conditions were developed for the synthesis of both diastereomers of tertiary homoallylic alcohols. Treatment of camphor N-tosylpyrazolidinone derived alpha-ketoamides with allyltributylstannane afforded both the individual homoallylic alcohols in high optical purity (up to 98% de) when the reaction was carried out in the presence of Sn(OTf)(2) and PdCl2, respectively. The stereochemical outcome and reversal of stereoselectivity in the reaction are proposed based on C-13 NMR and FTIR studies. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:887 / 893
页数:7
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