Mechanistic rationalization of organocatalyzed conjugate addition of linear aldehydes to nitro-olefins

J. Bures; A. Armstrong; D. G. Blackmond

doi:10.1021/ja203660r

Mechanistic rationalization of organocatalyzed conjugate addition of linear aldehydes to nitro-olefins

J. Bures
, A. Armstrong
, D. G. Blackmond

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

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Abstract

Kinetic studies of the conjugate addition of propanal to nitrostyrene catalyzed by diarylprolinol ethers reveal that formation of the product iminium species is rate-determining and is promoted by both the reaction product and acid additives. The beneficial role of a dominant cyclobutane intermediate in maintaining high stereoselectivity is highlighted. This mechanistic understanding led to the design of highly productive reaction protocols.

Original language	English
Pages (from-to)	8822-8825
Number of pages	4
Journal	J Am Chem Soc
Volume	133
DOIs	https://doi.org/10.1021/ja203660r
Publication status	Published - 2011

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Bures-2011-Mechanistic rationalization of orga

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title = "Mechanistic rationalization of organocatalyzed conjugate addition of linear aldehydes to nitro-olefins",

abstract = "Kinetic studies of the conjugate addition of propanal to nitrostyrene catalyzed by diarylprolinol ethers reveal that formation of the product iminium species is rate-determining and is promoted by both the reaction product and acid additives. The beneficial role of a dominant cyclobutane intermediate in maintaining high stereoselectivity is highlighted. This mechanistic understanding led to the design of highly productive reaction protocols.",

author = "J. Bures and A. Armstrong and Blackmond, \{D. G.\}",

note = "M1 - 23 Bures, Jordi Armstrong, Alan Blackmond, Donna G eng 2011/05/17 06:00 J Am Chem Soc. 2011 Jun 15;133(23):8822-5. doi: 10.1021/ja203660r. Epub 2011 May 18.",

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AU - Armstrong, A.

AU - Blackmond, D. G.

N1 - M1 - 23 Bures, Jordi Armstrong, Alan Blackmond, Donna G eng 2011/05/17 06:00 J Am Chem Soc. 2011 Jun 15;133(23):8822-5. doi: 10.1021/ja203660r. Epub 2011 May 18.

PY - 2011

Y1 - 2011

N2 - Kinetic studies of the conjugate addition of propanal to nitrostyrene catalyzed by diarylprolinol ethers reveal that formation of the product iminium species is rate-determining and is promoted by both the reaction product and acid additives. The beneficial role of a dominant cyclobutane intermediate in maintaining high stereoselectivity is highlighted. This mechanistic understanding led to the design of highly productive reaction protocols.

AB - Kinetic studies of the conjugate addition of propanal to nitrostyrene catalyzed by diarylprolinol ethers reveal that formation of the product iminium species is rate-determining and is promoted by both the reaction product and acid additives. The beneficial role of a dominant cyclobutane intermediate in maintaining high stereoselectivity is highlighted. This mechanistic understanding led to the design of highly productive reaction protocols.

U2 - 10.1021/ja203660r

DO - 10.1021/ja203660r

M3 - Article

SN - 1520-5126

VL - 133

SP - 8822

EP - 8825

JO - J Am Chem Soc

JF - J Am Chem Soc

ER -

Mechanistic rationalization of organocatalyzed conjugate addition of linear aldehydes to nitro-olefins

Abstract

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