New insights into the endo-exo stereoselectivity of the intramolecular Diels-Alder reaction of 1,3,8-nonatrienes

被引：31

作者：

Lilly, MJ

Paddon-Row, MN ^{[1
]}

Sherburn, MS

Turner, CI

机构：

[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia

[2] Massey Univ, Inst Fundamental Sci, Palmerston North, New Zealand

[3] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia

来源：

CHEMICAL COMMUNICATIONS | 2000年 / 22期

关键词：

D O I：

10.1039/b006483l

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

B3LYP/6-31G(d) theory predicts the experimental endo-exo selectivity of intramolecular Diels-Alder reactions of C9-substituted 1,3,8-nonatrienes: the reactions are concerted but the transition structures are remarkably asynchronous.

引用

页码：2213 / 2214

页数：2

共 14 条

[1] [Anonymous], 1991, Comprehensive Organic Synthesis
[2] THE USE OF DICHLOROMALEIC AND BROMOMALEIC ANHYDRIDES IN THE SYNTHESIS OF LACTONES BY THE INTRAMOLECULAR DIELS-ALDER REACTION
BATCHELOR, MJ
MELLOR, JM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (05): : 985 - 995
[3] A THEORETICAL-STUDY OF INTRAMOLECULAR DIELS-ALDER AND 1,3-DIPOLAR CYCLOADDITION STEREOSELECTIVITY USING ABINITIO METHODS, SEMIEMPIRICAL METHODS, AND A TANDEM QUANTUM MECHANIC MOLECULAR MECHANIC METHOD
BROWN, FK
SINGH, UC
KOLLMAN, PA
RAIMONDI, L
HOUK, KN
BOCK, CW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (18) : 4862 - 4869
[4] THE INFLUENCE OF SUBSTITUENT INDUCED ASYNCHRONICITY ON THE STEREOCHEMISTRIES OF INTRAMOLECULAR DIELS-ALDER REACTIONS
BROWN, FK
HOUK, KN
[J]. TETRAHEDRON LETTERS, 1985, 26 (19) : 2297 - 2300
[5] STEREOCHEMICAL ASPECTS OF THE INTRAMOLECULAR DIELS-ALDER REACTION
CRAIG, D
[J]. CHEMICAL SOCIETY REVIEWS, 1987, 16 (02) : 187 - 238
[6] Experimental determination of the activation parameters and stereoselectivities of the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene and transition state modeling with the Monte Carlo-Jumping between Wells/molecular dynamics method
Diedrich, MK
Klarner, FG
Beno, BR
Houk, KN
Senderowitz, H
Still, WC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (43) : 10255 - 10259
[7] LILLY MJ, 1997, CHEM COMMUN, P687
[8] Total synthesis of (-)-solanapyrone A via enzymatic Diels-Alder reaction of prosolanapyrone
Oikawa, H
Kobayashi, T
Katayama, K
Suzuki, Y
Ichihara, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) : 8748 - 8756
[9] EMPIRICAL FORCE-FIELD MODELS FOR THE TRANSITION-STATES OF INTRAMOLECULAR DIELS-ALDER REACTIONS BASED UPON ABINITIO TRANSITION STRUCTURES
RAIMONDI, L
BROWN, FK
GONZALEZ, J
HOUK, KN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (12) : 4796 - 4804
[10] STEREOCHEMICAL ASPECTS OF THE INTRAMOLECULAR DIELS-ALDER REACTIONS OF METHYL DECA-2,7,9-TRIENOATES .1. THERMAL CYCLIZATIONS
ROUSH, WR
KO, AI
GILLIS, HR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (21) : 4264 - 4267

← 1 2 →