Highly efficient synthesis of α,β-acetylenic aldehydes from terminal alkynes using DMF as the formylating reagent.

被引:91
作者
Journet, M [1 ]
Cai, DW [1 ]
DiMichele, LM [1 ]
Larsen, RD [1 ]
机构
[1] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA
关键词
D O I
10.1016/S0040-4039(98)01352-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The formylation of lithium acetylides with DMF led to alpha,beta-acetylenic aldehydes in excellent yields (>94%). A reverse quench into a phosphate buffer (10% aqueous KH2PO4 ,4 equiv) proved ro he the key for this high-yielding reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6427 / 6428
页数:2
相关论文
共 15 条
[1]   THE ROLE OF CHELATION IN THE FORMYLATION OF GRIGNARD-REAGENTS WITH N-FORMYL AMINES [J].
AMARATUNGA, W ;
FRECHET, JMJ .
TETRAHEDRON LETTERS, 1983, 24 (11) :1143-1146
[2]  
COMINS D, 1978, SYNTHESIS-STUTTGART, P403
[3]   Enantioselective Diels-Alder reactions between cyclopentadiene and alpha,beta-acetylenic aldehydes catalyzed by a chiral super Lewis acid [J].
Corey, EJ ;
Lee, TW .
TETRAHEDRON LETTERS, 1997, 38 (33) :5755-5758
[4]   A convenient one-pot method for the construction of tetrasubstituted phenols through a Michael addition aldol cyclization sequence [J].
CovarrubiasZuniga, A ;
RiosBarrios, E .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5688-5689
[5]   First enantioselective catalytic Diels-Alder reaction of dienes and acetylenic aldehydes: Experimental and theoretical evidence for the predominance of exo-transition structure [J].
Ishihara, K ;
Kondo, S ;
Kurihara, H ;
Yamamoto, H ;
Ohashi, S ;
Inagaki, S .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) :3026-3027
[6]   RESEARCHES ON ACETYLENIC COMPOUNDS .60. THE SYNTHESIS OF 3 NATURAL POLYACETYLENIC HYDROCARBONS [J].
JONES, ERH ;
SKATTEBOL, L ;
WHITING, MC .
JOURNAL OF THE CHEMICAL SOCIETY, 1958, (MAR) :1054-1059
[7]   SYNTHESIS OF MACROCYCLIC PROPARGYLIC ALCOHOLS BY ENE-TYPE CYCLIZATION OF UNSATURATED ACETYLENIC ALDEHYDES [J].
MARSHALL, JA ;
ANDERSEN, MW .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2766-2768
[8]   CEMBRANOLIDE TOTAL SYNTHESIS - MACROCYCLIZATION OF (ALPHA-ALKOXYALLYL)STANNANE ACETYLENIC ALDEHYDES AS A ROUTE TO CEMBRANE LACTONES [J].
MARSHALL, JA ;
CROOKS, SL ;
DEHOFF, BS .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1616-1623
[9]  
MIKAMI K, 1993, SYNLETT, P23
[10]   INTRAMOLECULAR 11-(3,4) ENE APPROACH TO THE BICYCLIC CORE OF ENEDIYNE ANTIBIOTICS - DYNEMICIN, CALICHEAMICIN, AND ESPERAMICIN [J].
MIKAMI, K ;
MATSUEDA, H ;
NAKAI, T .
TETRAHEDRON LETTERS, 1993, 34 (22) :3571-3572