A chiral probe for the asynchronous transition state of Diels-Alder reactions with acetylenedicarboxylate

被引：8

作者：

Buckle, RN ^{[1
]}

Burnell, DJ ^{[1
]}

机构：

[1] Mem Univ Newfoundland, Dept Chem, St Johns, NF A1B 3X7, Canada

来源：

TETRAHEDRON | 1999年 / 55卷 / 52期

关键词：

Diels-Alder reactions; diastereoselection; alkynes;

D O I：

10.1016/S0040-4020(99)00982-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diels-Alder reactions took place with modest diastereoselectivity between dimethylcyclohexadiene derivative 3a and di-(-)-menthyl acetylenedicarboxylate. whereas the dimethylcydohexadiene 2 showed no selectivity whatsoever. These results can be rationalized in terms of a complete lack of any endo-exo preference for the carboxylate groups and a more synchronous addition with 3a than with 2. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：14829 / 14838

页数：10

共 21 条

[1] STEREODIVERGENT DIELS-ALDER REACTIONS EMPLOYING CYCLITOLS AS CHIRAL AUXILIARIES
AKIYAMA, T
HORIGUCHI, N
IDA, T
OZAKI, S
[J]. CHEMISTRY LETTERS, 1995, (11) : 975 - 976
[2] Differences in rates of Diels-Alder reactions as experimental indicators of synchronous or asynchronous transition states
Buckle, RN
Liu, PY
Roberts, EWD
Burnell, DJ
[J]. TETRAHEDRON, 1999, 55 (38) : 11455 - 11464
[3] Use of 9-anthrylcarbinol derivatives as chiral auxiliaries in asymmetric Diels-Alder reaction
Carriere, A
Virgili, A
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (01) : 227 - 230
[4] SYNTHESIS OF ACETYLENEDICARBOXYLIC ACID-ESTERS AND ASYMMETRIC DIELS-ALDER REACTIONS OF THE BIS(METHYL (S)-LACTYL) ESTER
CHARLTON, JL
CHEE, G
MCCOLEMAN, H
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1995, 73 (09): : 1454 - 1462
[5] ASYMMETRIC-SYNTHESIS OF PODOPHYLLOTOXIN ANALOGS
CHARLTON, JL
PLOURDE, GL
KOH, K
SECCO, AS
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1990, 68 (11): : 2022 - 2027
[6] AN ASYMMETRIC-SYNTHESIS OF 2-AMINO-6,7-DIHYDROXY-1,2,3,4-TETRAHYDRONAPHTHALENE (ADTN)
CHARLTON, JL
KOH, K
PLOURDE, GL
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1990, 68 (11): : 2028 - 2032
[7] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL
DEWAR, MJS
ZOEBISCH, EG
HEALY, EF
STEWART, JJP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) : 3902 - 3909
[8] ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES
EVANS, DA
CHAPMAN, KT
BISAHA, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) : 1238 - 1256
[9] EVNS SV, 1988, ACTA CRYSTALLOGR C, V44, P880
[10] Theoretical studies of Diels-Alder reactions of acetylenic compounds
Froese, RDJ
Coxon, JM
West, SC
Morokuma, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) : 6991 - 6996

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