Iminium-allenamine cascade catalysis: One-pot access to chiral 4Hchromenes by a highly enantioselective michael-michael sequence

Xinshuai Zhang; Shilei Zhang; Wei Wang

doi:10.1002/anie.200906050

Iminium-allenamine cascade catalysis: One-pot access to chiral 4Hchromenes by a highly enantioselective michael-michael sequence

Xinshuai Zhang, Shilei Zhang, Wei Wang

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

135 Scopus citations

Abstract

Chemical Equation Presented Taking the Michael-Michael: A cascade Michael-Michael reaction of aryl or alkyl alkynals, involving an unprecedented iminium - allenamine sequence, is efficiently catalyzed by a chiral diphenylprolinol TBDMS ether, and affords highly functionalized 4H-chromenes in high yields. TBDMS = tert-butyldimethylsilyl.

Original language	English (US)
Pages (from-to)	1481-1484
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	8
DOIs	https://doi.org/10.1002/anie.200906050
State	Published - Feb 15 2010
Externally published	Yes

Keywords

Alkynal
Cascade reactions
Enantioselectivity
Michael addition
Organocatalysis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200906050

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title = "Iminium-allenamine cascade catalysis: One-pot access to chiral 4Hchromenes by a highly enantioselective michael-michael sequence",

abstract = "Chemical Equation Presented Taking the Michael-Michael: A cascade Michael-Michael reaction of aryl or alkyl alkynals, involving an unprecedented iminium - allenamine sequence, is efficiently catalyzed by a chiral diphenylprolinol TBDMS ether, and affords highly functionalized 4H-chromenes in high yields. TBDMS = tert-butyldimethylsilyl.",

keywords = "Alkynal, Cascade reactions, Enantioselectivity, Michael addition, Organocatalysis",

author = "Xinshuai Zhang and Shilei Zhang and Wei Wang",

year = "2010",

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doi = "10.1002/anie.200906050",

language = "English (US)",

volume = "49",

pages = "1481--1484",

journal = "Angewandte Chemie - International Edition",

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T1 - Iminium-allenamine cascade catalysis

T2 - One-pot access to chiral 4Hchromenes by a highly enantioselective michael-michael sequence

AU - Zhang, Xinshuai

AU - Zhang, Shilei

AU - Wang, Wei

PY - 2010/2/15

Y1 - 2010/2/15

N2 - Chemical Equation Presented Taking the Michael-Michael: A cascade Michael-Michael reaction of aryl or alkyl alkynals, involving an unprecedented iminium - allenamine sequence, is efficiently catalyzed by a chiral diphenylprolinol TBDMS ether, and affords highly functionalized 4H-chromenes in high yields. TBDMS = tert-butyldimethylsilyl.

AB - Chemical Equation Presented Taking the Michael-Michael: A cascade Michael-Michael reaction of aryl or alkyl alkynals, involving an unprecedented iminium - allenamine sequence, is efficiently catalyzed by a chiral diphenylprolinol TBDMS ether, and affords highly functionalized 4H-chromenes in high yields. TBDMS = tert-butyldimethylsilyl.

KW - Alkynal

KW - Cascade reactions

KW - Enantioselectivity

KW - Michael addition

KW - Organocatalysis

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DO - 10.1002/anie.200906050

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VL - 49

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 8

ER -

Iminium-allenamine cascade catalysis: One-pot access to chiral 4Hchromenes by a highly enantioselective michael-michael sequence

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

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