Enantioselective Synthesis of (R)-Homoboroproline from (S)-Proline Using a Borylation Approach

被引：9

作者：

Georgiou, Irene ^{[1
]}

Whiting, Andrew ^{[1
]}

机构：

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

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 22期

关键词：

Aldol reactions; Boron; Enantioselectivity; Amino acids; Asymmetric synthesis; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; COPPER-CATALYZED BORYLATION; ASYMMETRIC DEPROTONATIONS; ESTERS; REAGENTS; BORATION; BIS(PINACOLATO)DIBORON; DIBORATION; LITHIATION; MECHANISM;

D O I：

10.1002/ejoc.201200652

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(S)-Proline was converted through a five-step sequence into (R)-homoboroproline hydrochloride in 29?% overall yield with 97?%?ee The key step was the conversion of N-Boc iodomethylpyrrolidine into the corresponding pinacol boronate ester by an efficient copper(I)-catalyzed borylation reaction by using bispinacolatodiboron.

引用

页码：4110 / 4113

页数：4

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