Amine-catalyzed coupling of aldehydes and ketenes derived from Fischer carbene complexes:: Formation of β-lactones and enol ethers

被引：14

作者：

Merlic, CA ^{[1
]}

Doroh, BC ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

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

关键词：

D O I：

10.1021/jo034476n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aldehydes react with ketenes generated from photolysis of Fischer chromium carbene complexes to generate either beta-lactones or enol ethers resulting from decarboxylation of beta-lactones. The reaction is catalyzed by tertiary amines and can occur with diastereoselectivity greater than 20:1 with DMAP as the catalyst.

引用

页码：6056 / 6059

页数：4

共 46 条

[1] STEREOSPECIFIC INTRODUCTION OF DOUBLE-BONDS VIA THERMOLYSIS OF BETA-LACTONES
ADAM, W
BAEZA, J
LIU, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (06) : 2000 - &
[2] [Anonymous], [No title captured]
[3] The total synthesis of (-)-tetrahydrolipstatin
Bodkin, JA
Humphries, EJ
McLeod, MD
[J]. TETRAHEDRON LETTERS, 2003, 44 (14) : 2869 - 2872
[4] BOSE AK, 1974, TETRAHEDRON LETT, V15, P2633
[5] Functionalised β-lactones from chromium alkyl(alkoxy)carbene complexes
Caldwell, JJ
Kerr, WJ
McKendry, S
[J]. TETRAHEDRON LETTERS, 1999, 40 (17) : 3485 - 3486
[6] Catalytic, asymmetric dimerization of methylketene
Calter, MA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) : 8006 - 8007
[7] CASEY CP, 1973, TETRAHEDRON LETT, V14, P1421
[8] The first preparation of β-lactones by radical cyclization
Castle, K
Hau, CS
Sweeney, JB
Tindall, C
[J]. ORGANIC LETTERS, 2003, 5 (05) : 757 - 759
[9] SYNTHESIS OF BETA-LACTONES BY THE PHOTOCHEMICAL-REACTIONS OF CHROMIUM ALKOXYCARBENE COMPLEXES WITH ALDEHYDES
COLSON, PJ
HEGEDUS, LS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) : 4972 - 4976
[10] Cortez GS, 2001, SYNTHESIS-STUTTGART, P1731

← 1 2 3 4 5 →