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
收藏
页码：875 / 878
页数：4
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