A (-)-sparteine-directed highly enantioselective synthesis of boroproline.: Solid- and solution-state structure and properties

被引：27

作者：

Batsanov, Andrei S. ^{[1
]}

Grosjean, Christophe ^{[1
]}

Schuetz, Thorben ^{[1
]}

Whiting, Andrew ^{[1
]}

机构：

[1] Univ Durham, Dept Chem, Sci Labs, Durham DH1 3LE, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 16期

关键词：

D O I：

10.1021/jo0708792

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A two-step, direct asymmetric synthesis of the trifluoroacetate ammonium salt of boroproline is reported. (-)-Sparteine-mediated lithiation of N-Boc-pyrrolidine afforded N-Boc-aminoboronic acid in good yield and enantioselectivity as determined by HPLC (pinanediol ester). Deprotection using TFA yielded the ammonium salt; full characterization data are presented, and the structure in aqueous solution and the occurrence of a B-N species are discussed.

引用

页码：6276 / 6279

页数：4

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