Deciphering the origin of stereoinduction in cooperative asymmetric catalysis involving Pd(II) and a chiral Bronsted acid

Jindal, Garima ; Sunoj, Raghavan B. (2015) Deciphering the origin of stereoinduction in cooperative asymmetric catalysis involving Pd(II) and a chiral Bronsted acid Organic Letters, 17 (12). pp. 2874-2877. ISSN 1523-7060

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Official URL: http://pubs.acs.org/doi/abs/10.1021/acs.orglett.5b...

Related URL: http://dx.doi.org/10.1021/acs.orglett.5b00860

Abstract

The density functional (M06) computations on a cooperative multicatalytic reaction involving palladium acetate and a chiral Bronsted acid in the conversion of an indenyl cyclobutanol to spirocyclic indene bearing a quaternary carbon ring junction are reported. A chiral Pd-bis-phosphate is identified as the active catalyst in the enantioselective ring expansion as compared to alternative possibilities wherein the chiral phosphate/phosphoric acid is in the outer sphere of palladium. The enantiocontrolling transition state exhibited more effective C–H•••π interactions, lower distortion of the catalyst and an orthogonal orientation of the bulky phosphate ligands.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:109711
Deposited On:02 Aug 2017 11:47
Last Modified:02 Aug 2017 11:47

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