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 50 条

[1] TRANSITION STATE OF DIELS-ALDER REACTIONS
LIU, MTH
SCHMIDT, C
TETRAHEDRON, 1971, 27 (22) : 5289 - &
[2] SYNCHRONICITY IN DIELS-ALDER REACTIONS REVISITED - HIGHLY ASYNCHRONOUS TRANSITION-STATES FOR SYMMETRICAL DIELS-ALDER REACTIONS
SINGLETON, DA
LEUNG, SW
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 208 : 403 - ORGN
[3] STEREOCHEMISTRY OF THE TRANSITION-STATE IN DIELS-ALDER REACTIONS
ELYANOV, BS
SHAKHOVA, SK
POLKOVNIKOV, BD
RAR, LA
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1979, 28 (11): : 2472 - 2473
[4] NATURE OF TRANSITION STATE IN SOME DIELS-ALDER REACTIONS
DEWAR, MJS
PYRON, RS
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (10) : 3098 - &
[5] ASYMMETRIC DIELS-ALDER REACTIONS WITH CHIRAL ALKOXYCYCLOHEXADIENES
BIRD, CW
LEWIS, A
TETRAHEDRON LETTERS, 1989, 30 (45) : 6227 - 6228
[6] Stereoselective Diels-Alder reactions of chiral anthracenes
Sanyal, A
Snyder, JK
ORGANIC LETTERS, 2000, 2 (16) : 2527 - 2530
[7] DIELS-ALDER REACTIONS OF TRIMETHYLSILOXY-SUBSTITUTED BUTADIENES WITH DIMETHYL ACETYLENEDICARBOXYLATE
YAMAMOTO, K
SUZUKI, S
TSUJI, J
CHEMISTRY LETTERS, 1978, (06) : 649 - 652
[8] DIELS-ALDER REACTIONS OF 1-CARBOMETHOXY-PYRROLES AND DIMETHYL ACETYLENEDICARBOXYLATE
GABEL, NW
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (01): : 301 - &
[9] On the method-dependence of transition state asynchronicity in Diels-Alder reactions
Linder, Mats
Brinck, Tore
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2013, 15 (14) : 5108 - 5114
[10] Differences in rates of Diels-Alder reactions as experimental indicators of synchronous or asynchronous transition states
Buckle, RN
Liu, PY
Roberts, EWD
Burnell, DJ
TETRAHEDRON, 1999, 55 (38) : 11455 - 11464

← 1 2 3 4 5 →