Cyclic imidate salts in acyclic stereochemistry: Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides
Reaction of 2-alkyl-4-enamides 1 with I + and aq. NaHCO 3 results in the diastereoselective formation of syn-iodohydrins 2, which are converted to the epoxides 3 with base. The reaction appears to proceed through a cyclic imidate type intermediate 4, followed by addition of water and ring opening. R...
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| Published in: | Tetrahedron Vol. 52; no. 9; pp. 3327 - 3338 |
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| Main Authors: | , , , , , , , , , , , |
| Format: | Journal Article |
| Language: | English |
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Elsevier Ltd
26-02-1996
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| Abstract | Reaction of 2-alkyl-4-enamides 1 with I
+ and aq. NaHCO
3 results in the diastereoselective formation of syn-iodohydrins 2, which are converted to the epoxides 3 with base. The reaction appears to proceed through a cyclic imidate type intermediate 4, followed by addition of water and ring opening.
Reaction of 2-alkyl-4-enamides with 1
+ 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). |
|---|---|
| AbstractList | Reaction of 2-alkyl-4-enamides 1 with I
+ and aq. NaHCO
3 results in the diastereoselective formation of syn-iodohydrins 2, which are converted to the epoxides 3 with base. The reaction appears to proceed through a cyclic imidate type intermediate 4, followed by addition of water and ring opening.
Reaction of 2-alkyl-4-enamides with 1
+ 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). |
| Author | Cianciosi, S.J. Weissman, S.A. Volante, R.P. Maligres, P.E. Sager, J. Reider, P.J. Eng, K.K. Purick, R.M. Upadhyay, V. Reamer, R.A. Askin, D. Rossen, K. |
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| Cites_doi | 10.1021/jo00101a002 10.1021/jo00036a004 10.1016/S0040-4039(00)94725-7 10.1021/jo01285a028 10.1021/ja00955a029 10.3987/R-1981-08-1291 10.1021/jo01015a036 10.1021/ja01027a033 10.1021/ja00316a044 10.1139/v75-394 10.1016/S0040-4039(00)75787-X 10.1021/jm00047a001 10.1016/0040-4039(95)00273-F 10.1016/0040-4020(84)80012-5 10.1021/ja01012a030 10.1021/ja00952a030 10.1039/C39920000728 10.1246/cl.1990.733 10.1016/0040-4039(95)00696-A 10.1016/S0040-4039(00)99848-4 10.1021/jo00098a012 10.1016/S0040-4020(01)86953-2 10.1016/S0040-4039(00)60916-4 10.1021/ja00201a035 |
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3 results in the diastereoselective formation of syn-iodohydrins 2, which are converted to the epoxides... |
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| SubjectTerms | Enamide Epoxidation Imidate Indinavir Iodohydrin |
| Title | Cyclic imidate salts in acyclic stereochemistry: Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides |
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