Highly enantioselective formal aza-Diels-Alder reactions with acylhydrazones and Danishefsky's diene promoted by a silicon Lewis acid

Sharon K. Lee; Uttam K. Tambar; Nicholas R. Perl; James L. Leighton

doi:10.1016/j.tet.2010.03.036

Highly enantioselective formal aza-Diels-Alder reactions with acylhydrazones and Danishefsky's diene promoted by a silicon Lewis acid

Sharon K. Lee, Uttam K. Tambar, Nicholas R. Perl, James L. Leighton

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

27 Scopus citations

Abstract

Silicon Lewis acid 3 is effective for the promotion of highly enantioselective cycloaddition reactions of acylhydrazones with Danishefsky's diene (formal aza-Diels-Alder reactions). The reactions are conducted at ambient temperature for 15 min, and produce the products in good yield and with high levels of enantioselectivity. A remarkable solvent-dependent reversal in the sense of absolute stereochemical induction has been observed. The method has been applied to an efficient and stereoselective synthesis of the neurokinin 1 receptor antagonist casopitant.

Original language	English (US)
Pages (from-to)	4769-4774
Number of pages	6
Journal	Tetrahedron
Volume	66
Issue number	26
DOIs	https://doi.org/10.1016/j.tet.2010.03.036
State	Published - Jun 26 2010

Keywords

Acylhydrazones
Aza-Diels-Alder
Casopitant
Danishefsky's Diene
Silicon Lewis Acid

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2010.03.036

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title = "Highly enantioselective formal aza-Diels-Alder reactions with acylhydrazones and Danishefsky's diene promoted by a silicon Lewis acid",

abstract = "Silicon Lewis acid 3 is effective for the promotion of highly enantioselective cycloaddition reactions of acylhydrazones with Danishefsky's diene (formal aza-Diels-Alder reactions). The reactions are conducted at ambient temperature for 15 min, and produce the products in good yield and with high levels of enantioselectivity. A remarkable solvent-dependent reversal in the sense of absolute stereochemical induction has been observed. The method has been applied to an efficient and stereoselective synthesis of the neurokinin 1 receptor antagonist casopitant.",

keywords = "Acylhydrazones, Aza-Diels-Alder, Casopitant, Danishefsky's Diene, Silicon Lewis Acid",

author = "Lee, {Sharon K.} and Tambar, {Uttam K.} and Perl, {Nicholas R.} and Leighton, {James L.}",

note = "Funding Information: This work was supported by a grant from the National Science Foundation ( CHE-08-09659 ). S.K.L. is a National Science Foundation Graduate Research Fellow and U.K.T. is a National Institutes of Health Postdoctoral Fellow (F32 GM077937). We thank Boehringer-Ingelheim for a Graduate Fellowship to N.R.P.",

year = "2010",

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doi = "10.1016/j.tet.2010.03.036",

language = "English (US)",

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pages = "4769--4774",

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T1 - Highly enantioselective formal aza-Diels-Alder reactions with acylhydrazones and Danishefsky's diene promoted by a silicon Lewis acid

AU - Lee, Sharon K.

AU - Tambar, Uttam K.

AU - Perl, Nicholas R.

AU - Leighton, James L.

N1 - Funding Information: This work was supported by a grant from the National Science Foundation ( CHE-08-09659 ). S.K.L. is a National Science Foundation Graduate Research Fellow and U.K.T. is a National Institutes of Health Postdoctoral Fellow (F32 GM077937). We thank Boehringer-Ingelheim for a Graduate Fellowship to N.R.P.

PY - 2010/6/26

Y1 - 2010/6/26

N2 - Silicon Lewis acid 3 is effective for the promotion of highly enantioselective cycloaddition reactions of acylhydrazones with Danishefsky's diene (formal aza-Diels-Alder reactions). The reactions are conducted at ambient temperature for 15 min, and produce the products in good yield and with high levels of enantioselectivity. A remarkable solvent-dependent reversal in the sense of absolute stereochemical induction has been observed. The method has been applied to an efficient and stereoselective synthesis of the neurokinin 1 receptor antagonist casopitant.

AB - Silicon Lewis acid 3 is effective for the promotion of highly enantioselective cycloaddition reactions of acylhydrazones with Danishefsky's diene (formal aza-Diels-Alder reactions). The reactions are conducted at ambient temperature for 15 min, and produce the products in good yield and with high levels of enantioselectivity. A remarkable solvent-dependent reversal in the sense of absolute stereochemical induction has been observed. The method has been applied to an efficient and stereoselective synthesis of the neurokinin 1 receptor antagonist casopitant.

KW - Acylhydrazones

KW - Aza-Diels-Alder

KW - Casopitant

KW - Danishefsky's Diene

KW - Silicon Lewis Acid

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U2 - 10.1016/j.tet.2010.03.036

DO - 10.1016/j.tet.2010.03.036

M3 - Article

AN - SCOPUS:77954244845

SN - 0040-4020

VL - 66

SP - 4769

EP - 4774

JO - Tetrahedron

JF - Tetrahedron

IS - 26

ER -

Highly enantioselective formal aza-Diels-Alder reactions with acylhydrazones and Danishefsky's diene promoted by a silicon Lewis acid

Abstract

Keywords

ASJC Scopus subject areas

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