Enantioselective intramolecular formal [2 + 4] annulation of acrylates and α,β-unsaturated imines catalyzed by amino acid derived phosphines

Zhichao Jin; Ruojie Yang; Yu Du; Bhoopendra Tiwari; Rakesh Ganguly; Yonggui Robin Chi

doi:10.1021/ol3013588

Enantioselective intramolecular formal [2 + 4] annulation of acrylates and α,β-unsaturated imines catalyzed by amino acid derived phosphines

Zhichao Jin, Ruojie Yang, Yu Du, Bhoopendra Tiwari, Rakesh Ganguly, Yonggui Robin Chi^*

^*Corresponding author for this work

Nanyang Technological University

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

80 Citations (Scopus)

Abstract

The first chiral phosphine-catalyzed activation of acrylates for intramolecular formal [2 + 4] reactions with unsaturated imines is described. The catalytic reactions afford N-heterocycles with exceptionally high diastereo- and enantioselectivities. The [2 + 4] products are amenable for further transformations to useful molecules such as chiral piperidines and multicyclic structures.

Original language	English
Pages (from-to)	3226-3229
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	12
DOIs	https://doi.org/10.1021/ol3013588
Publication status	Published - Jun 15 2012
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol3013588

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abstract = "The first chiral phosphine-catalyzed activation of acrylates for intramolecular formal [2 + 4] reactions with unsaturated imines is described. The catalytic reactions afford N-heterocycles with exceptionally high diastereo- and enantioselectivities. The [2 + 4] products are amenable for further transformations to useful molecules such as chiral piperidines and multicyclic structures.",

author = "Zhichao Jin and Ruojie Yang and Yu Du and Bhoopendra Tiwari and Rakesh Ganguly and Chi, {Yonggui Robin}",

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AU - Jin, Zhichao

AU - Yang, Ruojie

AU - Du, Yu

AU - Tiwari, Bhoopendra

AU - Ganguly, Rakesh

AU - Chi, Yonggui Robin

PY - 2012/6/15

Y1 - 2012/6/15

N2 - The first chiral phosphine-catalyzed activation of acrylates for intramolecular formal [2 + 4] reactions with unsaturated imines is described. The catalytic reactions afford N-heterocycles with exceptionally high diastereo- and enantioselectivities. The [2 + 4] products are amenable for further transformations to useful molecules such as chiral piperidines and multicyclic structures.

AB - The first chiral phosphine-catalyzed activation of acrylates for intramolecular formal [2 + 4] reactions with unsaturated imines is described. The catalytic reactions afford N-heterocycles with exceptionally high diastereo- and enantioselectivities. The [2 + 4] products are amenable for further transformations to useful molecules such as chiral piperidines and multicyclic structures.

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Enantioselective intramolecular formal [2 + 4] annulation of acrylates and α,β-unsaturated imines catalyzed by amino acid derived phosphines

Abstract

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