Reversing Enantioselectivity Using Noncovalent Interactions in Asymmetric Dearomatization of β-Naphthols: The Power of 3,3′ Substituents in Chiral Phosphoric Acid Catalysts

被引：34
|
作者：
Changotra, Avtar [1 ]
Das, Sandip [1 ]
Sunoj, Raghavan B. [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 09期
关键词：
BRONSTED-ACID; RING OPENINGS; MECHANISM; STEREOSELECTIVITY; DESYMMETRIZATION; CYCLIZATION; SELECTIVITY; ACTIVATION; ORIGINS; ESTERS;
D O I：
10.1021/acs.orglett.7b00890
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The sense of enantioselectivity in asymmetric dearomative amination of beta-naphthols is reported to pivotally depend on the 3,3' substituents on the chiral BINOL- phosphoric acid (CPA) catalysts. The origin of reversal in the sense of stereoinduction from R to S, when the aryl substituent is changed from 3,5-(CF3)(2)-C6H3 (CPA-1) to 9-anthryl (CPA-2), has been identified as arising due to the change in the pattern of noncovalent interactions (from predominantly C-H center dot center dot center dot F to C-H center dot center dot center dot pi interactions) in the stereocontrolling transition states.
引用
收藏
页码：2354 / 2357
页数：4
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