Reversing enantioselectivity using noncovalent interactions in asymmetric dearomatization of β-naphthols: the power of 3,3′ substituents in chiral phosphoric acid catalysts

Changotra, Avtar ; Das, Sandip ; Sunoj, Raghavan B. (2017) Reversing enantioselectivity using noncovalent interactions in asymmetric dearomatization of β-naphthols: the power of 3,3′ substituents in chiral phosphoric acid catalysts Organic Letters, 19 (9). pp. 2354-2357. ISSN 1523-7060

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Official URL: http://pubs.acs.org/doi/abs/10.1021/acs.orglett.7b...

Related URL: http://dx.doi.org/10.1021/acs.orglett.7b00890

Abstract

The sense of enantioselectivity in asymmetric dearomative amination of β-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•••F to C–H•••π interactions) in the stereocontrolling transition states.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:109677
Deposited On:02 Aug 2017 11:44
Last Modified:02 Aug 2017 11:44

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