Stereoselective synthesis of furans by the Pd-catalyzed Oshima-Utimoto reaction

被引:31
作者
Evans, MA [1 ]
Morken, JP [1 ]
机构
[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
关键词
D O I
10.1021/ol051275s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Pd-catalyzed coupling of acyclic allylic alcohols with vinyl ethers was examined and found to proceed with 2.5-10 mol % of catalyst and to provide cyclic acetals with good stereoselection. The reaction is tolerant of a number of functional groups and can be used to generate quaternary centers in a stereoselective fashion.
引用
收藏
页码:3367 / 3370
页数:4
相关论文
共 16 条
[1]   Natural sesquiterpenoids [J].
Fraga, BM .
NATURAL PRODUCT REPORTS, 2004, 21 (05) :669-693
[2]   ONE-POT SYNTHESIS OF TETRAHYDROFURAN DERIVATIVES FROM ALLYLIC ALCOHOLS AND VINYL ETHERS BY MEANS OF PALLADIUM(II) ACETATE [J].
FUGAMI, K ;
OSHIMA, K ;
UTIMOTO, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (06) :2050-2054
[3]   ONE-POT SYNTHESIS OF TETRAHYDROFURAN DERIVATIVES FROM ALLYLIC ALCOHOLS AND VINYL ETHERS BY MEANS OF PALLADIUM(II) ACETATE [J].
FUGAMI, K ;
OSHIMA, K ;
UTIMOTO, K .
TETRAHEDRON LETTERS, 1987, 28 (07) :809-812
[4]   ACID-INDUCED TRANSFORMATION OF PALLADIUM(0) BENZOQUINONE COMPLEXES TO PALLADIUM(II) AND HYDROQUINONE [J].
GRENNBERG, H ;
GOGOLL, A ;
BACKVALL, JE .
ORGANOMETALLICS, 1993, 12 (05) :1790-1793
[5]  
HAFNER W, 1966, LIEBIGS ANN CHEM, P109
[7]  
HOSOKAWA T, 1992, HETEROCYCLES, V33, P1079
[8]   OZONOLYSIS OF ENOL ETHERS - FORMATION OF 3-ALKOXY-1,2-DIOXOLANES BY CONCERTED ADDITION OF A CARBONYL OXIDE TO AN ENOL ETHER [J].
KEUL, H ;
CHOI, HS ;
KUCZKOWSKI, RL .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (18) :3365-3371
[9]  
Koch S. S. C., 1995, STUD NAT PROD CHEM, V16, P687
[10]   A DIRECT SYNTHESIS OF HYDROXYSEMPEROSIDE DEGLUCOSIDE [J].
KRAUS, GA ;
THURSTON, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) :9203-9205