A simple, user-friendly process for the homologation of aldehydes using tosylhydrazone salts

被引:31
作者
Aggarwal, VK
de Vicente, J
Pelotier, B
Holmes, IP
Bonnert, RV
机构
[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England
[2] AstraZeneca R&D Charnwood, Med Chem, Loughborough LE11 5RH, Leics, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4039(00)01856-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aldehydes can be homologated to ketones in moderate to good yields using aryldiazomethanes generated in situ from tosylhydrazones. Chiral aldehydes can be employed with almost complete retention of configuration. The tosylhydrazones can also be generated in situ from the corresponding aldehyde leading to a one-pot process for coupling two different carbonyl compounds to give ketones. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:10327 / 10331
页数:5
相关论文
共 17 条
[1]   Catalytic asymmetric epoxidation of aldehydes. Optimization, mechanism, and discovery of stereoelectronic control involving a combination of anomeric and Cieplak effects in sulfur ylide epoxidations with chiral 1,3-oxathianes [J].
Aggarwal, VK ;
Ford, JG ;
Fonquerna, S ;
Adams, H ;
Jones, RVH ;
Fieldhouse, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (33) :8328-8339
[2]  
AGGARWAL VK, UNPUB ANGEW CHEM INT
[3]  
AOYAMA T, 1988, SYNTHESIS-STUTTGART, P228
[4]   RING EXPANSION OF CYCLOBUTANONES TO CYCLOPENTANONES VIA ALPHA-LITHIOALKYL ARYL SULFOXIDES AND SELENOXIDES [J].
GADWOOD, RC ;
MALLICK, IM ;
DEWINTER, AJ .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (05) :774-782
[5]   A SELECTIVE METHOD FOR THE DIRECT CONVERSION OF ALDEHYDES INTO BETA-KETO-ESTERS WITH ETHYL DIAZOACETATE CATALYZED BY TIN(II) CHLORIDE [J].
HOLMQUIST, CR ;
ROSKAMP, EJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (14) :3258-3260
[6]   General and efficient insertions of carbons carrying aryl and heteroaryl groups: Synthesis of alpha-aryl- and alpha-heteroaryl-substituted ketones [J].
Katritzky, AR ;
Toader, D ;
Xie, LH .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21) :7571-7577
[7]   GENERAL AND EFFICIENT CARBON INSERTION ROUTE TO ONE-CARBON-HOMOLOGATED ALPHA-ARYL, ALPHA-ALKENYL, ALPHA-ALKOXY, AND ALPHA-PHENYLTHIO ALKYL KETONES [J].
KATRITZKY, AR ;
XIE, LH ;
TOADER, D ;
SERDYUK, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (48) :12015-12016
[8]   LITHIUM BROMIDE CATALYZED HOMOLOGATION OF ALDEHYDES WITH ARYLDIAZOMETHANES [J].
LOESCHORN, CA ;
NAKAJIMA, M ;
MCCLOSKEY, PJ ;
ANSELME, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23) :4407-4410
[9]   Iron Lewis acid catalyzed reactions of phenyldiazomethane with aromatic aldehydes [J].
Mahmood, SJ ;
Saha, AK ;
Hossain, MM .
TETRAHEDRON, 1998, 54 (3-4) :349-358
[10]   Iron Lewis acid catalyzed reactions of aromatic aldehydes with ethyl diazoacetate: Unprecedented formation of 3-hydroxy-2-arylacrylic acid ethyl esters by a unique 1,2-aryl shift [J].
Mahmood, SJ ;
Hossain, MM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3333-3336