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

43 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",

number = "9",

}

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

UR - https://www.scopus.com/pages/publications/0030065870

UR - https://www.scopus.com/pages/publications/0030065870#tab=citedBy

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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