Issue 7, 2012
From the journal:

Chemical Communications

Asymmetric [3+2] annulation of allenes with maleimides catalyzed by dipeptide-derived phosphines: facile creation of functionalized bicyclic cyclopentenes containing two tertiary stereogenic centers†

Qianyi Zhao,a   Xiaoyu Han,b   Yin Wei,c   Min Shi*ac  and  Yixin Lu*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

b Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Republic of Singapore
E-mail: chmlyx@nus.edu.sg

c 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

D-Threonine-L-tert-leucine-derived bifunctional phosphine, Cat. 11, catalyzed highly enantioselective [3+2] annulation of maleimides with allenes has been disclosed, allowing the synthesis of optically active functionalized bicyclic cyclopentenes containing two tertiary stereogenic centers in good to high yields along with good to high enantioselectivities.

Graphical abstract: Asymmetric [3+2] annulation of allenes with maleimides catalyzed by dipeptide-derived phosphines: facile creation of functionalized bicyclic cyclopentenes containing two tertiary stereogenic centers

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Article information

DOI
https://doi.org/10.1039/C2CC16904E
Article type
Communication
Submitted
08 Nov 2011
Accepted
23 Nov 2011
First published
24 Nov 2011

Chem. Commun., 2012,48, 970-972

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Asymmetric [3+2] annulation of allenes with maleimides catalyzed by dipeptide-derived phosphines: facile creation of functionalized bicyclic cyclopentenes containing two tertiary stereogenic centers

Q. Zhao, X. Han, Y. Wei, M. Shi and Y. Lu, Chem. Commun., 2012, 48, 970 DOI: 10.1039/C2CC16904E

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