Rhodium-catalyzed 1,4-addition of alkenylzirconocene chlorides to electron deficient alkenes

被引：25

作者：

Kakuuchi, A ^{[1
]}

Taguchi, T ^{[1
]}

Hanzawa, Y ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 06期

关键词：

D O I：

10.1016/j.tet.2003.08.073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1,4-conjugated addition of alkenylzirconocene chloride complexes to alpha,beta-enones, alpha,beta-enoic acid esters, and alpha,beta-enoic acid amides can be efficiently achieved by the use of [RhCl(cod)](2) catalyst. A high diastereoselectivity (95% yield, 90% de) was obtained through the reaction of alpha,beta-enoic acid amide derived from Oppolzer's sultam and 2-butenoyl chloride, while the use of Evans' chiral oxazolidinone as a chiral auxiliary in place of Oppolzer's sultam, gave a poor diastereoselectivity (98% yield, 26% de). (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：1293 / 1299

页数：7

共 50 条

[1] Rhodium-catalyzed 1,4-addition reactions of diboron reagents to electron deficient olefins
Kabalka, GW
Das, BC
Das, S
TETRAHEDRON LETTERS, 2002, 43 (13) : 2323 - 2325
[2] Rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids and their derivatives to electron deficient olefins
Hayashi, T
SYNLETT, 2001, : 879 - 887
[3] Heteroarylboronates in Rhodium-Catalyzed 1,4-Addition to Enones
Albrecht, Fabian
Sowada, Oliver
Fistikci, Meryem
Boysen, Mike M. K.
ORGANIC LETTERS, 2014, 16 (19) : 5212 - 5215
[4] Rhodium-catalyzed asymmetric 1,4-addition of organometallic reagents
T. Hayashi
Russian Chemical Bulletin, 2003, 52 : 2595 - 2605
[5] Rhodium-catalyzed asymmetric 1,4-addition of organometallic reagents
Hayashi, T
RUSSIAN CHEMICAL BULLETIN, 2003, 52 (12) : 2595 - 2605
[6] Rhodium-catalyzed asymmetric 1,4-addition to 1-alkenylphosphonates
Hayashi, T
Senda, T
Takaya, Y
Ogasawara, M
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) : 11591 - 11592
[7] Rhodium-catalyzed 1,4-addition of terminal alkynes to vinyl ketones
Lerum, RV
Chisholm, JD
TETRAHEDRON LETTERS, 2004, 45 (35) : 6591 - 6594
[8] A Rhodium-Catalyzed Tandem Alkyne Dimerization/1,4-Addition Reaction
Lerum, Ronald V.
Russo, Christopher M.
Marquez, Jocellie E.
Chisholm, John D.
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (17) : 3485 - 3491
[9] Rhodium-Catalyzed Asymmetric 1,4-Addition of α/β-(N-Indolyl) Acrylates
Tan, Shuting
Liu, Jian-Guo
Xu, Ming-Hua
ORGANIC LETTERS, 2022, 24 (51) : 9349 - 9354
[10] Rhodium-catalyzed asymmetric 1,4-addition of arylboron reagents to α,β-unsaturated esters
Takaya, Y
Senda, T
Kurushima, H
Ogasawara, M
Hayashi, T
TETRAHEDRON-ASYMMETRY, 1999, 10 (20) : 4047 - 4056

← 1 2 3 4 5 →