Highly diastereoselective reaction of a chiral, non-racemic amide enolate with (S)-glycidyl tosylate. Synthesis of the orally active HIV-1 protease inhibitor L-735,524

David Askin; Kan K. Eng; Kai Rossen; Robert M. Purick; Kenneth M. Wells; R. P. Volante; Paul J. Reider

doi:10.1016/S0040-4039(00)75787-X

Highly diastereoselective reaction of a chiral, non-racemic amide enolate with (S)-glycidyl tosylate. Synthesis of the orally active HIV-1 protease inhibitor L-735,524

David Askin, Kan K. Eng, Kai Rossen, Robert M. Purick, Kenneth M. Wells, R. P. Volante, Paul J. Reider

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

159 Scopus citations

Abstract

Reaction of chiral amide enolate Li-1 with (S)-glycidyl tosylate 11 affords the epoxide 3 in 72% yield with high diastereoselectivity. Epoxide 3 is converted to the orally-active HIV-1 protease inhibitor L-735,524 in 71% isolated yield.

Original language	English (US)
Pages (from-to)	673-676
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	5
DOIs	https://doi.org/10.1016/S0040-4039(00)75787-X
State	Published - 1994
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)75787-X

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title = "Highly diastereoselective reaction of a chiral, non-racemic amide enolate with (S)-glycidyl tosylate. Synthesis of the orally active HIV-1 protease inhibitor L-735,524",

abstract = "Reaction of chiral amide enolate Li-1 with (S)-glycidyl tosylate 11 affords the epoxide 3 in 72% yield with high diastereoselectivity. Epoxide 3 is converted to the orally-active HIV-1 protease inhibitor L-735,524 in 71% isolated yield.",

author = "David Askin and Eng, {Kan K.} and Kai Rossen and Purick, {Robert M.} and Wells, {Kenneth M.} and Volante, {R. P.} and Reider, {Paul J.}",

year = "1994",

doi = "10.1016/S0040-4039(00)75787-X",

language = "English (US)",

volume = "35",

pages = "673--676",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "5",

}

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T1 - Highly diastereoselective reaction of a chiral, non-racemic amide enolate with (S)-glycidyl tosylate. Synthesis of the orally active HIV-1 protease inhibitor L-735,524

AU - Askin, David

AU - Eng, Kan K.

AU - Rossen, Kai

AU - Purick, Robert M.

AU - Wells, Kenneth M.

AU - Volante, R. P.

AU - Reider, Paul J.

PY - 1994

Y1 - 1994

N2 - Reaction of chiral amide enolate Li-1 with (S)-glycidyl tosylate 11 affords the epoxide 3 in 72% yield with high diastereoselectivity. Epoxide 3 is converted to the orally-active HIV-1 protease inhibitor L-735,524 in 71% isolated yield.

AB - Reaction of chiral amide enolate Li-1 with (S)-glycidyl tosylate 11 affords the epoxide 3 in 72% yield with high diastereoselectivity. Epoxide 3 is converted to the orally-active HIV-1 protease inhibitor L-735,524 in 71% isolated yield.

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U2 - 10.1016/S0040-4039(00)75787-X

DO - 10.1016/S0040-4039(00)75787-X

M3 - Article

AN - SCOPUS:0028147531

SN - 0040-4039

VL - 35

SP - 673

EP - 676

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 5

ER -

Highly diastereoselective reaction of a chiral, non-racemic amide enolate with (S)-glycidyl tosylate. Synthesis of the orally active HIV-1 protease inhibitor L-735,524

Abstract

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