Cyclic imidate salts in acyclic stereochemistry: Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides

P. E. Maligres; S. A. Weissman; V. Upadhyay; S. J. Cianciosi; R. A. Reamer; R. M. Purick; J. Sager; K. Rossen; K. K. Eng; D. Askin; R. P. Volante; P. J. Reider

doi:10.1016/0040-4020(95)01114-5

Cyclic imidate salts in acyclic stereochemistry: Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides

P. E. Maligres, S. A. Weissman, V. Upadhyay, S. J. Cianciosi, R. A. Reamer, R. M. Purick, J. Sager, K. Rossen, K. K. Eng, D. Askin, R. P. Volante, P. J. Reider

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

42 Scopus citations

Abstract

Reaction of 2-alkyl-4-enamides with I⁺ and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins with essentially no iodolactone by-product. The reaction appears to proceed through a cyclic imidate type intermediate. This methodology has been successfully employed for the synthesis of the epoxide intermediate of the orally active HIV-1 protease inhibitor MK-639 (indinavir sulfate).

Original language	English (US)
Pages (from-to)	3327-3338
Number of pages	12
Journal	Tetrahedron
Volume	52
Issue number	9
DOIs	https://doi.org/10.1016/0040-4020(95)01114-5
State	Published - Feb 26 1996
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

enamide
epoxidation
imidate
indinavir
iodohydrin

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10.1016/0040-4020(95)01114-5

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Maligres, P. E., Weissman, S. A., Upadhyay, V., Cianciosi, S. J., Reamer, R. A., Purick, R. M., Sager, J., Rossen, K., Eng, K. K., Askin, D., Volante, R. P., & Reider, P. J. (1996). Cyclic imidate salts in acyclic stereochemistry: Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides. Tetrahedron, 52(9), 3327-3338. https://doi.org/10.1016/0040-4020(95)01114-5

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title = "Cyclic imidate salts in acyclic stereochemistry: Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides",

abstract = "Reaction of 2-alkyl-4-enamides with I+ and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins with essentially no iodolactone by-product. The reaction appears to proceed through a cyclic imidate type intermediate. This methodology has been successfully employed for the synthesis of the epoxide intermediate of the orally active HIV-1 protease inhibitor MK-639 (indinavir sulfate).",

keywords = "enamide, epoxidation, imidate, indinavir, iodohydrin",

author = "Maligres, {P. E.} and Weissman, {S. A.} and V. Upadhyay and Cianciosi, {S. J.} and Reamer, {R. A.} and Purick, {R. M.} and J. Sager and K. Rossen and Eng, {K. K.} and D. Askin and Volante, {R. P.} and Reider, {P. J.}",

year = "1996",

month = feb,

day = "26",

doi = "10.1016/0040-4020(95)01114-5",

language = "English (US)",

volume = "52",

pages = "3327--3338",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

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TY - JOUR

T1 - Cyclic imidate salts in acyclic stereochemistry

T2 - Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides

AU - Maligres, P. E.

AU - Weissman, S. A.

AU - Upadhyay, V.

AU - Cianciosi, S. J.

AU - Reamer, R. A.

AU - Purick, R. M.

AU - Sager, J.

AU - Rossen, K.

AU - Eng, K. K.

AU - Askin, D.

AU - Volante, R. P.

AU - Reider, P. J.

PY - 1996/2/26

Y1 - 1996/2/26

N2 - Reaction of 2-alkyl-4-enamides with I+ and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins with essentially no iodolactone by-product. The reaction appears to proceed through a cyclic imidate type intermediate. This methodology has been successfully employed for the synthesis of the epoxide intermediate of the orally active HIV-1 protease inhibitor MK-639 (indinavir sulfate).

AB - Reaction of 2-alkyl-4-enamides with I+ and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins with essentially no iodolactone by-product. The reaction appears to proceed through a cyclic imidate type intermediate. This methodology has been successfully employed for the synthesis of the epoxide intermediate of the orally active HIV-1 protease inhibitor MK-639 (indinavir sulfate).

KW - enamide

KW - epoxidation

KW - imidate

KW - indinavir

KW - iodohydrin

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U2 - 10.1016/0040-4020(95)01114-5

DO - 10.1016/0040-4020(95)01114-5

M3 - Article

AN - SCOPUS:0030065870

SN - 0040-4020

VL - 52

SP - 3327

EP - 3338

JO - Tetrahedron

JF - Tetrahedron

IS - 9

ER -

Cyclic imidate salts in acyclic stereochemistry: Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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