Chiral glycine cation equivalents:: N-acyliminium species derived from diketopiperazines

被引：22

作者：

Bull, SD ^{[1
]}

Davies, SG ^{[1
]}

Garner, AC ^{[1
]}

O'Shea, MD ^{[1
]}

Savory, ED ^{[1
]}

Snow, EJ ^{[1
]}

机构：

[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 22期

关键词：

D O I：

10.1039/b207457p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Studies towards a N,N'-bis(p-methoxybenzyl) diketopiperazine asymmetric glycine cation equivalent for the synthesis of homochiral alpha-amino acids are described. The oxidation of enolate 3 with molecular oxygen provides either a mixture of hydroxylated diketopiperazines 7 and 8 or trione 10 depending upon the reaction conditions. The nucleophilic reduction of trione 10 and the reaction of acetoxy N-acyliminium ion precursors 5 and 6, derived from 7 and 8, with allyltrimethylsilane and boron trifluoride etherate is examined and a model for the stereoselectivity observed in these additions is presented.

引用

页码：2442 / 2448

页数：7

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