Steric factors direct Baylis-Hillman and aldol reactions in titanium tetrachloride mediated coupling between α-keto esters and cyclohex-2-enone derivatives

被引：54

作者：

Basavaiah, D ^{[1
]}

Sreenivasulu, B ^{[1
]}

Rao, AJ ^{[1
]}

机构：

[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 15期

关键词：

D O I：

10.1021/jo0342424

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The titanium tetrachloride mediated reaction of a-keto esters with 5,5-dimethylcyclohex-2-enone provides the corresponding Baylis-Hillman adducts exclusively whereas a similar reaction of a-keto esters with cyclohex-2-enone furnishes the corresponding aldol adducts (with high syn-diasteroe-selectivity) as the major product (along with the Baylis-Hillman adducts as the minor product), thus clearly demonstrating the role of the steric factors in directing the reaction pathway.

引用

页码：5983 / 5991

页数：9

共 46 条

[1] Correlation between pKa and reactivity of quinuclidine-based catalysts in the Baylis-Hillman reaction:: Discovery of quinuclidine as optimum catalyst leading to substantial enhancement of scope
Aggarwal, VK
Emme, I
Fulford, SY
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) : 692 - 700
[2] An easy and stereoselective synthesis of N-Boc-dolaproine via the Baylis-Hillman reaction
Almeida, WP
Coelho, F
[J]. TETRAHEDRON LETTERS, 2003, 44 (05) : 937 - 940
[3] SYNTHESIS OF POLYFUNCTIONAL GAMMA-LACTAMS AND PERHYDRO-1,2-PYRIDAZIN-3-ONES
AMRI, H
ELGAIED, MM
BENAYED, T
VILLIERAS, J
[J]. TETRAHEDRON LETTERS, 1992, 33 (48) : 7345 - 7346
[4] Synthesis of chiral bicyclic azetidine derivatives
Barrett, AGM
Dozzo, P
White, AJP
Williams, DJ
[J]. TETRAHEDRON, 2002, 58 (36) : 7303 - 7313
[5] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction
Basavaiah, D
Rao, PD
Hyma, RS
[J]. TETRAHEDRON, 1996, 52 (24) : 8001 - 8062
[6] First example of electrophile induced Baylis-Hillman reaction: a novel facile one-pot synthesis of indolizine derivatives
Basavaiah, D
Rao, AJ
[J]. CHEMICAL COMMUNICATIONS, 2003, (05) : 604 - 605
[7] The Baylis-Hillman reaction: One-pot facile synthesis of 2,4-functionalized 1,4-pentadienes
Basavaiah, D
Sharada, DS
Kumaragurubaran, N
Reddy, RM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) : 7135 - 7137
[8] One-pot facile conversion of the acetates of Baylis-Hillman adducts into substituted fused pyrimidones in aqueous media
Basavaiah, D
Satyanarayana, T
[J]. TETRAHEDRON LETTERS, 2002, 43 (24) : 4301 - 4303
[9] A novel and facile synthesis of functionalized [4.4.3] and [4.4.4] propellano-bislactones using acetates of the Baylis-Hillman adducts
Basavaiah, D
Satyanarayana, T
[J]. ORGANIC LETTERS, 2001, 3 (23) : 3619 - 3622
[10] A SIMPLE SYNTHESIS OF ALPHA-METHYLENE-BETA-HYDROXYALKANONES
BASAVAIAH, D
GOWRISWARI, VVL
[J]. TETRAHEDRON LETTERS, 1986, 27 (18) : 2031 - 2032

← 1 2 3 4 5 →