Carbohydrates as chiral auxiliaries in asymmetric darzens reactions: Enantioselective synthesis of the benzothiazepine ring system of diltiazem

被引:0
作者
Nangia, A
Rao, PB
Madhavi, NNL
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来源
JOURNAL OF CHEMICAL RESEARCH-S | 1996年 / 07期
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O6 [化学];
学科分类号
0703 ;
摘要
Darzens condensation of a dihydroglucal chloro ester 18 with p-anisaldehyde affords diastereoisomeric glycidic esters 20,21 which are elaborated to the benzothiazepinone ring system 25 of diltiazem 1.
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页码:312 / 313
页数:3
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共 24 条
[1]  
AKITA H, 1989, CHEM PHARM BULL, V37, P2876
[2]   PYRANOSIDULOSES .8. RAPID ROUTE TO HEX-1-ENOPYRAN-3-ULOSES [J].
FRASERREID, B ;
WALKER, DL ;
TAM, SYK ;
HOLDER, NL .
CANADIAN JOURNAL OF CHEMISTRY, 1973, 51 (23) :3950-3954
[3]   REACTION OF 3-PHENYLGLYCIDIC ESTERS .2. STEREO-SELECTIVITY AND REGIO-SELECTIVITY IN THE OXIRANE RING-OPENING OF METHYL TRANS-3-(4-METHOXYPHENYL)GLYCIDATE WITH VARIOUS THIOPHENOLS AND THE EFFECTS OF SOLVENT AND TEMPERATURE [J].
HASHIYAMA, T ;
INOUE, H ;
TAKEDA, M ;
AOE, K ;
KOTERA, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (03) :421-427
[4]   REACTION OF 3-PHENYLGLYCIDIC ESTERS .1. STEREOSELECTIVE OPENING OF THE OXIRANE RING OF TRANS-3-PHENYLGLYCIDIC ESTERS WITH 2-NITROTHIOPHENOLS AND THE EFFECT OF VARIOUS CATALYSTS THEREON [J].
HASHIYAMA, T ;
INOUE, H ;
KONDA, M ;
TAKEDA, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (08) :1725-1732
[5]  
IGARASHI K, 1968, TETRAHEDRON LETT, P751
[6]   LIPASE CATALYSIS IN THE RESOLUTION OF RACEMIC INTERMEDIATES OF DILTIAZEM SYNTHESIS IN ORGANIC-SOLVENTS [J].
KANERVA, LT ;
SUNDHOLM, O .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (13) :1385-1389
[7]  
Kikuo I., 1984, Ger. Pat., Patent No. [3.415.035, 3415035]
[8]   ABSOLUTE CONFORMATION AND CONFIGURATION OF (2S, 3S)-3-ACETOXY-5-(DIMETHYLAMINOETHYL)-2-(4-METHOXYPHENYL)-2,3-DIHYDRO-1,5-BENZOTHIAZEPIN-4(5H)-ONE CHLORIDE (DILTHIAZEM HYDROCHLORIDE) [J].
KOJICPRODIC, B ;
RUZICTOROS, Z ;
SUNJIC, V ;
DECORTE, E ;
MOIMAS, F .
HELVETICA CHIMICA ACTA, 1984, 67 (03) :916-926
[9]  
KUGITA H, 1971, CHEM PHARM BULL, V19, P595
[10]   CARBOHYDRATES AS CHIRAL AUXILIARIES IN STEREOSELECTIVE SYNTHESIS [J].
KUNZ, H ;
RUCK, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (03) :336-358