Issue 32, 2013
From the journal:

Chemical Communications

A Pd(ii)-catalyzed asymmetric approach toward chiral [3.3.1]-bicyclic ketals using 2-hydroxyphenylboronic acid as a pro-bis(nucleophile)†

Feijun Wang,*a   Feng Chen,a   Mingliang Qu,a   Teng Li,a   Yunlong Liua  and  Min Shi*ab  

* Corresponding authors

a Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 MeiLong Road, Shanghai 200237, P. R. China
E-mail: feijunwang@ecust.edu.cn

b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. China
E-mail: mshi@mail.sioc.ac.cn

Abstract

Enantioselective Pd(II)-catalyzed construction of [3.3.1]-bicyclic ketals from 2-hydroxyphenylboronic acid 1 and enone 3 is reported, yielding enantioenriched [3.3.1]-bicyclic ketals in up to 97% yields and 98% ee.

Graphical abstract: A Pd(ii)-catalyzed asymmetric approach toward chiral [3.3.1]-bicyclic ketals using 2-hydroxyphenylboronic acid as a pro-bis(nucleophile)

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Article information

DOI
https://doi.org/10.1039/C3CC00295K
Article type
Communication
Submitted
13 Jan 2013
Accepted
07 Mar 2013
First published
07 Mar 2013

Chem. Commun., 2013,49, 3360-3362

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A Pd(II)-catalyzed asymmetric approach toward chiral [3.3.1]-bicyclic ketals using 2-hydroxyphenylboronic acid as a pro-bis(nucleophile)

F. Wang, F. Chen, M. Qu, T. Li, Y. Liu and M. Shi, Chem. Commun., 2013, 49, 3360 DOI: 10.1039/C3CC00295K

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