C2-Symmetric bipyrrolidines as organocatalysts for asymmetric Diels-Alder reactions

Yuanhui Ma; Yong Jian Zhang; Shangbin Jin; Qiqi Li; Chenguang Li; Junseong Lee; Wanbin Zhang

doi:10.1016/j.tetlet.2009.10.067

C₂-Symmetric bipyrrolidines as organocatalysts for asymmetric Diels-Alder reactions

Yuanhui Ma
, Yong Jian Zhang
, Shangbin Jin
, Qiqi Li
, Chenguang Li
, Junseong Lee
, Wanbin Zhang

Shanghai Jiao Tong University
University of Utah

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

A new class of C₂-symmetric 3,3′-dialkoxy-2,2′-bipyrrolidines have been designed and developed for asymmetric organocatalytic Diels-Alder reactions of α,β-unsaturated aldehydes. The bipyrrolidines combined with HClO₄ were found to be effective organocatalysts for enantioselective Diels-Alder reactions. The catalysis mode has been demonstrated by NMR and X-ray crystallographic studies for diiminium intermediate.

Original language	English
Pages (from-to)	7388-7391
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	52
DOIs	https://doi.org/10.1016/j.tetlet.2009.10.067
State	Published - 30 Dec 2009
Externally published	Yes

Keywords

Bipyrrolidines
C-Symmetry
Diels-Alder reaction
Organocatalyst

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10.1016/j.tetlet.2009.10.067

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title = "C2-Symmetric bipyrrolidines as organocatalysts for asymmetric Diels-Alder reactions",

abstract = "A new class of C2-symmetric 3,3′-dialkoxy-2,2′-bipyrrolidines have been designed and developed for asymmetric organocatalytic Diels-Alder reactions of α,β-unsaturated aldehydes. The bipyrrolidines combined with HClO4 were found to be effective organocatalysts for enantioselective Diels-Alder reactions. The catalysis mode has been demonstrated by NMR and X-ray crystallographic studies for diiminium intermediate.",

keywords = "Bipyrrolidines, C-Symmetry, Diels-Alder reaction, Organocatalyst",

author = "Yuanhui Ma and Zhang, \{Yong Jian\} and Shangbin Jin and Qiqi Li and Chenguang Li and Junseong Lee and Wanbin Zhang",

year = "2009",

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day = "30",

doi = "10.1016/j.tetlet.2009.10.067",

language = "英语",

volume = "50",

pages = "7388--7391",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - C2-Symmetric bipyrrolidines as organocatalysts for asymmetric Diels-Alder reactions

AU - Ma, Yuanhui

AU - Zhang, Yong Jian

AU - Jin, Shangbin

AU - Li, Qiqi

AU - Li, Chenguang

AU - Lee, Junseong

AU - Zhang, Wanbin

PY - 2009/12/30

Y1 - 2009/12/30

N2 - A new class of C2-symmetric 3,3′-dialkoxy-2,2′-bipyrrolidines have been designed and developed for asymmetric organocatalytic Diels-Alder reactions of α,β-unsaturated aldehydes. The bipyrrolidines combined with HClO4 were found to be effective organocatalysts for enantioselective Diels-Alder reactions. The catalysis mode has been demonstrated by NMR and X-ray crystallographic studies for diiminium intermediate.

AB - A new class of C2-symmetric 3,3′-dialkoxy-2,2′-bipyrrolidines have been designed and developed for asymmetric organocatalytic Diels-Alder reactions of α,β-unsaturated aldehydes. The bipyrrolidines combined with HClO4 were found to be effective organocatalysts for enantioselective Diels-Alder reactions. The catalysis mode has been demonstrated by NMR and X-ray crystallographic studies for diiminium intermediate.

KW - Bipyrrolidines

KW - C-Symmetry

KW - Diels-Alder reaction

KW - Organocatalyst

UR - https://www.scopus.com/pages/publications/70449133493

U2 - 10.1016/j.tetlet.2009.10.067

DO - 10.1016/j.tetlet.2009.10.067

M3 - 文章

AN - SCOPUS:70449133493

SN - 0040-4039

VL - 50

SP - 7388

EP - 7391

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 52

ER -

C₂-Symmetric bipyrrolidines as organocatalysts for asymmetric Diels-Alder reactions

Abstract

Keywords

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