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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