Synthesis and resolution of a novel chiral diamine ligand and application to asymmetric lithiation-substitution

被引：62

作者：

Li, XL ^{[1
]}

Schenkel, LB ^{[1
]}

Kozlowski, MC ^{[1
]}

机构：

[1] Univ Penn, Roy & Diana Vagelos Labs, Dept Chem, Philadelphia, PA 19104 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 07期

关键词：

D O I：

10.1021/ol9903133

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A short, efficient synthesis of chiral 1,5-diaza-cis-decalins (7) is presented. In the lithiation of N-Boc pyrrolidine, the ligands with the smallest most electron rich R groups (Me > Et > (CH2Bu)-Bu-t > CH2CF3 approximate to Bn) were most effective. In the asymmetric deprotonation/substitution of benzylic substrates, (R,R)-7 (R = Me, R' = H) conferred modest selectivity. The ready availability of both enantiomers of the 1,5-diaza-cis-decalins and the ability to tune steric and electronic properties renders these compounds an attractive new class of diamine ligands.

引用

页码：875 / 878

页数：4

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