Manganese(III)-promoted free radical cyclizations of enamides leading to beta-lactams

被引：28

作者：

DAnnibale, A

Pesce, A

Resta, S

Trogolo, C

机构：

[1] Ctro. C.N.R. Stud. Chim. Sostanze O., Dipartimento di Chimica, Univ. Studi di Roma La Sapienza, P.le Aldo Moro 5

来源：

TETRAHEDRON | 1997年 / 53卷 / 38期

关键词：

D O I：

10.1016/S0040-4020(97)00835-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of variously substituted enamides with Mn(OAc)(3) . 2H(2)O afforded beta-lactamic products in modest to good yields, depending mostly on the solvent and reaction conditions. The substitution pattern of the enamidic double bond was found of primary importance for the outcome of the reaction. (C) 1997 Published by Elsevier Science Ltd.

引用

页码：13129 / 13138

页数：10

共 19 条

[1] NEW SYNTHESIS OF LACTAMS AND SPIROLACTAMS RADICAL CYCLIZATION INDUCED BY MANGANESE(III) ACETATE
COSSY, J
LEBLANC, C
[J]. TETRAHEDRON LETTERS, 1989, 30 (34) : 4531 - 4534
[2] COSSY J, 1993, SYNLETT, P202
[3] Ceric ammonium nitrate promoted free radical cyclization reactions leading to beta-lactams
DAnnibale, A
Pesce, A
Resta, S
Trogolo, C
[J]. TETRAHEDRON LETTERS, 1997, 38 (10) : 1829 - 1832
[4] MN(III) - PROMOTED CYCLIZATION OF ENAMIDES - AN OXIDATIVE RADICAL APPROACH TO BETA-LACTAMS
DANNIBALE, A
RESTA, S
TROGOLO, C
[J]. TETRAHEDRON LETTERS, 1995, 36 (49) : 9039 - 9042
[5] Reaction of 2,2,6-trimethyl-4H-1,3-dioxin-4-one with imines: An easy route to enamides.
DAnnibale, A
Pesce, A
Resta, S
Trogolo, C
[J]. TETRAHEDRON LETTERS, 1996, 37 (41) : 7429 - 7432
[6] FREE-RADICAL CYCLIZATIONS LEADING TO 4-MEMBERED RINGS .1. BETA-LACTAM PRODUCTION USING TRIBUTYLTIN HYDRIDE
FREMONT, SL
BELLETIRE, JL
HO, DM
[J]. TETRAHEDRON LETTERS, 1991, 32 (21) : 2335 - 2338
[7] A convenient approach to diastereomerically pure 1,3,4-trisubstituted pyrrolidin-2-ones by intramolecular cyclisation of N-(2-alken-1-yl)amides mediated by Mn(III). An entry to both (R)- and (S)-3-pyrrolidineacetic acid
Galeazzi, R
Mobbili, G
Orena, M
[J]. TETRAHEDRON, 1996, 52 (03) : 1069 - 1084
[8] COBALT-MEDIATED REACTIONS - A NEW SYNTHETIC APPROACH TO BETA-LACTAM, GAMMA-LACTAM AND DELTA-LACTAM
GILL, GB
PATTENDEN, G
REYNOLDS, SJ
[J]. TETRAHEDRON LETTERS, 1989, 30 (24) : 3229 - 3232
[9] ISHIBASHI H, 1993, SYNLETT, P649
[10] SULFUR-DIRECTED REGIOSELECTIVE RADICAL CYCLIZATION LEADING TO BETA-LACTAMS - FORMAL SYNTHESIS OF (+/-)-PS-5 AND (+)-THIENAMYCIN
ISHIBASHI, H
KAMEOKA, C
IRIYAMA, H
KODAMA, K
SATO, T
IKEDA, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) : 1276 - 1284

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