Enantioselective protonation of samarium enolates derived from α-heterosubstituted ketones and lactone by SmI2-mediated reduction

被引:51
作者
Nakamura, Y
Takeuchi, S
Ohgo, Y
Yamaoka, M
Yoshida, A
Mikami, K
机构
[1] Niigata Coll Pharm, Niigata 9502081, Japan
[2] Tokyo Inst Technol, Dept Chem Technol, Meguro Ku, Tokyo 152, Japan
关键词
D O I
10.1016/S0040-4020(99)00143-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
SmI2-mediated reductive cleavage of alpha-hetero substituents of alpha-alkyl or alpha-aryl ketones and lactone gave the corresponding "thermodynamic samarium enolates". Enantioselective protonation of the samarium enolates with C-2-symmetric chiral diets afforded the corresponding ketones and lactone in moderate to high enantioselectivities. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4595 / 4620
页数:26
相关论文
共 90 条
[1]   PALLADIUM-MEDIATED ENANTIOSELECTIVE FORMATION OF 2-METHYLTETRAL-1-ONE FROM THE CORRESPONDING ALLYL OR BENZYL ENOL CARBONATE IN THE PRESENCE OF ENANTIOPURE AMINOALCOHOLS [J].
ABOULHODA, SJ ;
LETINOIS, S ;
WILKEN, J ;
REINERS, I ;
HENIN, F ;
MARTENS, J ;
MUZART, J .
TETRAHEDRON-ASYMMETRY, 1995, 6 (08) :1865-1868
[2]   β-amino tertiary cycloalkanols for the enantioselective protonation of enolic species produced by a palladium-induced cascade reaction [J].
Aboulhoda, SJ ;
Reiners, I ;
Wilken, J ;
Hénin, F ;
Martens, J ;
Muzart, J .
TETRAHEDRON-ASYMMETRY, 1998, 9 (11) :1847-1850
[3]   PRODUCTION OF OPTICALLY-ACTIVE KETONES BY A PALLADIUM-INDUCED CASCADE REACTION FROM RACEMIC BETA-KETOESTERS [J].
ABOULHODA, SJ ;
HENIN, F ;
MUZART, J ;
THOREY, C ;
BEHNEN, W ;
MARTENS, J ;
MEHLER, T .
TETRAHEDRON-ASYMMETRY, 1994, 5 (07) :1321-1326
[4]   Remarkable effect of lithium bromide in the enantioselective protonation with α-sulfinyl alcohols [J].
Asensio, G ;
Aleman, PA ;
Domingo, LR ;
Medio-Simón, M .
TETRAHEDRON LETTERS, 1998, 39 (20) :3277-3280
[5]   PINACOL-TYPE REARRANGEMENTS IN PHENYLCYCLOHEXANE SERIES - EVIDENCE FOR DIFFERENCES BETWEEN REACTION MECHANISMS OF EPOXIDES AND OF CORRESPONDING DIOLS AND HALOGENOHYDRINS [J].
BERTI, G ;
MACCHIA, B ;
MACCHIA, F ;
MONTI, L .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (20) :3371-&
[6]   NEW METHODS FOR PREPARATION OF 1-PHENYL-TRANS-CYCLOHEXANE-1,2-DIOL [J].
BERTI, G ;
BOTTARI, F ;
MACCHIA, B ;
MACCHIA, F .
TETRAHEDRON, 1965, 21 (12) :3277-&
[7]   THE CHEMISTRY OF THE TRITERPENES AND RELATED COMPOUNDS .18. ELUCIDATION OF THE STRUCTURE OF POLYPORENIC ACID-C [J].
BOWERS, A ;
HALSALL, TG ;
JONES, ERH ;
LEMIN, AJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1953, (SEP) :2548-2560
[8]   DERACEMIZATION OF SILYL ENOL ETHERS [J].
CAVELIER, F ;
GOMEZ, S ;
JACQUIER, R ;
VERDUCCI, J .
TETRAHEDRON-ASYMMETRY, 1993, 4 (12) :2501-2505
[9]   A FIRST APPROACH TO ASYMMETRIC PROTONATION VIA A POLYMER-SUPPORTED CHIRAL PROTON DONOR [J].
CAVELIER, F ;
GOMEZ, S ;
JACQUIER, R ;
VERDUCCI, J .
TETRAHEDRON LETTERS, 1994, 35 (18) :2891-2894
[10]   STUDIES IN STEREOCHEMISTRY .30. MODELS FOR STERIC CONTROL OF ASYMMETRIC INDUCTION [J].
CRAM, DJ ;
KOPECKY, KR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (11) :2748-2755