Stereoselective synthesis of 3-substituted phtalides via asymmetric transfer hydrogenation using well-defined ruthenium catalysts under neutral conditions

被引:57
作者
Everaere, K [1 ]
Scheffler, JL [1 ]
Mortreux, A [1 ]
Carpentier, JF [1 ]
机构
[1] ENSCL, Grp Chim Organ Appl, CNRS, Lab Catalyse Lille, F-59652 Villeneuve Dascq, France
关键词
asymmetric transfer hydrogenation; chiral phtalides; chiral Ru catalysts;
D O I
10.1016/S0040-4039(01)00076-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric transfer hydrogenation of methyl 2-acylbenzoates and 2-propyl 3-acetylpyridine- 2-carboxylate in 2-propanol, in the absence of base, with presynthesized Ru-{beta -amino alcohol) or Ru-{TsDPEN) true catalysts provides 3-alkylphtalides in high yields and 92-97% ee. The procedure is, however, not as efficient for the preparation of optically active 3-phenylphtalide. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1899 / 1901
页数:3
相关论文
共 27 条
[1]   CHIRAL AMINAL TEMPLATES .3. DIASTEREOSELECTIVITY OF ORGANOMETALLIC ATTACK ON ALDEHYDES BEARING A CHIRAL IMIDAZOLIDINE GROUP [J].
ALEXAKIS, A ;
SEDRANI, R ;
NORMANT, JF ;
MANGENEY, P .
TETRAHEDRON-ASYMMETRY, 1990, 1 (05) :283-286
[2]   REACTIONS OF CARBONYL-COMPOUNDS IN BASIC SOLUTIONS .13. THE MECHANISM OF THE ALKALINE-HYDROLYSIS OF 3-(3-SUBSTITUTED PHENOXY)PHTHALIDES, 3-METHYLPHTHALIDES, 3-PHENYLPHTHALIDES, NAPHTHALIDES, 3-PHENYLNAPTHALIDES, AND PHENANTHRALIDES, AND OF 3-SUBSTITUTED 3-METHOXYPHTHALIDES [J].
ANVIA, F ;
BOWDEN, K ;
ELKAISSI, FA ;
SAEZ, V .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (11) :1809-1814
[3]   STUDIES ON ORCHIDACEAE ALKALOIDS .14. A PHTHALIDE ALKALOID FROM DENDROBIUM PIERARDII ROXB [J].
ELANDER, M ;
LEANDER, K ;
LUNING, B .
ACTA CHEMICA SCANDINAVICA, 1969, 23 (06) :2177-&
[4]  
Everaere K, 2001, EUR J ORG CHEM, V2001, P275
[5]   N-benzyl-norephedrine derivatives as new, efficient ligands for ruthenium-catalyzed asymmetric transfer hydrogenation of functionalized ketones [J].
Everaere, K ;
Carpentier, JF ;
Mortreux, A ;
Bulliard, M .
TETRAHEDRON-ASYMMETRY, 1999, 10 (21) :4083-4086
[6]   The catalyst precursor, catalyst, and intermediate in the Ru-II-promoted asymmetric hydrogen transfer between alcohols and ketones [J].
Haack, KJ ;
Hashiguchi, S ;
Fujii, A ;
Ikariya, T ;
Noyori, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (03) :285-288
[7]   CENTRAL NERVOUS-SYSTEM ACTIVE COMPOUNDS .7. PHTHALIDE SYNTHESIS BY LITHIATION OF ALKOXYAROMATICS [J].
HUNG, TV ;
MOONEY, BA ;
PRAGER, RH ;
TIPPETT, JM .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (02) :383-395
[8]   RING-CHAIN TAUTOMERISM IN O-ACYLBENZOIC ACIDS . A COMPARISON OF EXPERIMENTAL METHODS AND A STUDY OF SUBSTITUENT EFFECTS [J].
JONES, PR ;
DESIO, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (12) :4293-&
[9]   Microbial asymmetric syntheses of 3-alkylphthalide derivatives [J].
Kitayama, T .
TETRAHEDRON-ASYMMETRY, 1997, 8 (22) :3765-3774
[10]   ANTIPROLIFERATIVE EFFECTS OF THE TRADITIONAL CHINESE MEDICINE SHIMOTSU-TO, ITS COMPONENT CNIDIUM RHIZOME AND DERIVED COMPOUNDS ON PRIMARY CULTURES OF MOUSE AORTA SMOOTH-MUSCLE CELLS [J].
KOBAYASHI, S ;
MIMURA, Y ;
NOTOYA, K ;
KIMURA, I ;
KIMURA, M .
JAPANESE JOURNAL OF PHARMACOLOGY, 1992, 60 (04) :397-401