Terminal alkyne-ethylene cross-metathesis: Reaction of 1-substituted propargyl esters at elevated ethylene pressure

被引:82
作者
Smulik, JA [1 ]
Diver, ST [1 ]
机构
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
关键词
D O I
10.1021/jo9916941
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Substituted propargylic esters, resistant to complete ethylene cross-metathesis at ambient pressure, underwent cross-metathesis with ethylene at elevated pressure (4 atm) to give a-substituted butadienes in good to excellent yields. Enantioenriched propargylic acetates, obtained through enzymatic kinetic resolution of secondary propargyl alcohols, similarly underwent ethylene metathesis with retention of stereochemistry at the chiral center.
引用
收藏
页码:1788 / 1792
页数:5
相关论文
共 29 条
[1]   ENANTIOSELECTIVE ESTERIFICATIONS OF UNSATURATED ALCOHOLS MEDIATED BY A LIPASE PREPARED FROM PSEUDOMONAS SP [J].
BURGESS, K ;
JENNINGS, LD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6129-6139
[2]   HIGHLY ENANTIOSELECTIVE ALKYNYLATION OF ALDEHYDES PROMOTED BY CHIRAL OXAZABOROLIDINES [J].
COREY, EJ ;
CIMPRICH, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3151-3152
[3]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO
[4]  
2-Z
[5]   ENANTIOSELECTIVE HYDROLYSES BY BAKERS-YEAST .3. MICROBIAL RESOLUTION OF ALKYNYL ESTERS USING LYOPHILIZED YEAST [J].
GLANZER, BI ;
FABER, K ;
GRIENGL, H .
TETRAHEDRON, 1987, 43 (24) :5791-5796
[6]   Recent advances in olefin metathesis and its application in organic synthesis [J].
Grubbs, RH ;
Chang, S .
TETRAHEDRON, 1998, 54 (18) :4413-4450
[7]   RING-CLOSING METATHESIS AND RELATED PROCESSES IN ORGANIC-SYNTHESIS [J].
GRUBBS, RH ;
MILLER, SJ ;
FU, GC .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (11) :446-452
[8]   PREPARATION OF RACEMIC AND CHIRAL ALKYL(1,3-BUTADIEN-2-YL)METHANOL DERIVATIVES UTILIZING 1-TRIMETHYLSILYL-2,3-BUTADIENE AS A DIENE SOURCE [J].
HATAKEYAMA, S ;
SUGAWARA, K ;
KAWAMURA, M ;
TAKANO, S .
TETRAHEDRON LETTERS, 1991, 32 (35) :4509-4512
[9]   A novel enantioselective synthesis of (+)-myriocin based on the chemistry of 1-trimethylsilylbuta-2,3-dienes [J].
Hatakeyama, S ;
Yoshida, M ;
Esumi, T ;
Iwabuchi, Y ;
Irie, H ;
Kawamoto, T ;
Yamada, H ;
Nishizawa, M .
TETRAHEDRON LETTERS, 1997, 38 (45) :7887-7890
[10]   METAL-CATALYZED REARRANGEMENT OF ALKENE ALKYNES AND THE STEREOCHEMISTRY OF METALLACYCLOBUTENE RING-OPENING [J].
KATZ, TJ ;
SIVAVEC, TM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (03) :737-738