LITHIUM CATALYZED HETERO-DIELS-ALDER REACTIONS CYCLOCONDENSATION OF N-PROTECTED ALPHA-AMINO ALDEHYDES WITH 1-METHOXY-3-TERT-BUTYLDIMETHYLSILYLOXYBUTADIENE IN THE PRESENCE OF LITHIUM PERCHLORATE

被引:37
作者
GRIECO, PA
MOHER, ED
机构
[1] Department of Chemistry Indiana University Bloomington
关键词
D O I
10.1016/S0040-4039(00)73883-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lithium perchlorate in diethyl ether catalyzes the cyclocondensation of N-BOC protected alpha-amino aldehydes with 1-methoxy-3-tert-butyldimethylsilyloxybutadiene providing, after exposure to acid, dihydropyrones possessing the threo configuration.
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页码:5567 / 5570
页数:4
相关论文
共 12 条
[1]   CRAM RULE SELECTIVITY IN THE LEWIS ACID-CATALYZED CYCLOCONDENSATION OF CHIRAL ALDEHYDES - A CONVENIENT ROUTE TO CHIRAL SYSTEMS OF BIOLOGICAL INTEREST [J].
DANISHEFSKY, S ;
KOBAYASHI, S ;
KERWIN, JF .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (10) :1981-1983
[2]   STEREODIVERGENT SYNTHESES OF THREO-6-AMINO-6-DEOXYHEPTOSULOSE AND ERYTHRO-6-AMINO-6-DEOXYHEPTOSULOSE DERIVATIVES VIA AN OPTICALLY-ACTIVE OXAZOLIDINE ALDEHYDE [J].
GARNER, P ;
RAMAKANTH, S .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (13) :2609-2612
[3]  
GOLEBIOWSKI A, 1986, HETEROCYCLES, V24, P1205
[4]   INFLUENCE OF N-PROTECTING GROUPS ON THE STEREOCHEMICAL COURSE OF [4+2] CYCLOADDITION OF ACTIVATED DIENES TO ALPHA-AMINO ALDEHYDES [J].
GOLEBIOWSKI, A ;
RACZKO, J ;
JACOBSSON, U ;
JURCZAK, J .
TETRAHEDRON, 1991, 47 (06) :1053-1064
[5]   EXPERIMENTS DIRECTED TOWARD THE TOTAL SYNTHESIS OF TERPENES .23. SYNTHESIS OF 4A-METHYL-4,4A,7,8-TETRAHYDRO-9H-BENZOCYCLOHEPTENE-2(3H),5(6H)-DIONE (B-HOMO WIELAND-MIESCHER KETONE) - VERSATILE INTERMEDIATE FOR TERPENE SYNTHESIS [J].
IRELAND, RE ;
ARISTOFF, PA ;
HOYNG, CF .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (24) :4318-4322
[6]   HIGH-PRESSURE (4+2)CYCLOADDITION OF 1-METHOXYBUTA-1,3-DIENE TO ALPHA-AMINO ALDEHYDES - INFLUENCE OF N-PROTECTING GROUPS ON ASYMMETRIC INDUCTION [J].
JURCZAK, J ;
GOLEBIOWSKI, A ;
RACZKO, J .
TETRAHEDRON LETTERS, 1988, 29 (46) :5975-5978
[7]   OPTICALLY-ACTIVE N-PROTECTED ALPHA-AMINO ALDEHYDES IN ORGANIC-SYNTHESIS [J].
JURCZAK, J ;
GOLEBIOWSKI, A .
CHEMICAL REVIEWS, 1989, 89 (01) :149-164
[8]  
JURCZAK J, 1989, J ORG CHEM, V54, P2496
[9]   STEREOSELECTIVE SYNTHESES OF ERYTHRO-BETA-AMINO AND THREO-BETA-AMINO ALCOHOL DERIVATIVES VIA HETERO-DIELS-ALDER REACTIONS [J].
MIDLAND, MM ;
AFONSO, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4368-4371
[10]   STEREOSELECTIVE SYNTHESIS OF BETA-AMINO ALCOHOLS FROM OPTICALLY-ACTIVE ALPHA-AMINO-ACIDS [J].
REETZ, MT ;
DREWES, MW ;
SCHMITZ, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (11) :1141-1143