STEREOSELECTIVE SYNTHESIS OF TETRAHYDROFURANS AND TETRAHYDROPYRANS BY NI(0) PROMOTED TANDEM CYCLIZATION-CARBONYLATION

被引:7
作者
DELGADO, A [1 ]
LLEBARIA, A [1 ]
CAMPS, F [1 ]
MORETO, JM [1 ]
机构
[1] CSIC,CID,DEPT QUIM ORGAN BIOL,E-08034 BARCELONA,SPAIN
关键词
D O I
10.1016/S0040-4039(00)76727-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of different vinyl bromides (1a-3a), beating phenyl substituted alkenyloxyalkyl groups, with Ni(CO)4 affords the corresponding substituted cyclic ethers 1b-3b in moderate to good yields and high diastereoselectivity. In the cyclization of 1a, the stereoselectivity of the process can be reversed by the use of additives, such as KOAc, TIOAc, Cs2CO3, and KOCOCF3.
引用
收藏
页码:4011 / 4014
页数:4
相关论文
共 14 条
[1]   PALLADIUM CATALYZED TANDEM CYCLIZATION-ANION CAPTURE PROCESSES .1. BACKGROUND AND HYDRIDE ION CAPTURE BY ALKYL-PALLADIUM AND PI-ALLYL-PALLADIUM SPECIES [J].
BURNS, B ;
GRIGG, R ;
SANTHAKUMAR, V ;
SRIDHARAN, V ;
STEVENSON, P ;
WORAKUN, T .
TETRAHEDRON, 1992, 48 (35) :7297-7320
[2]   TOTAL SYNTHESIS OF (+)-LYCORICIDINE AND ITS 2-EPIMER FROM D-GLUCOSE [J].
CHIDA, N ;
OHTSUKA, M ;
OGAWA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4441-4447
[3]   PALLADIUM CATALYZED CASCADE CYCLOADDITION REACTIONS - GENERAL CONCEPTS AND ILLUSTRATIVE EXAMPLES [J].
GRIGG, R ;
KENNEWELL, P ;
TEASDALE, A ;
SRIDHARAN, V .
TETRAHEDRON LETTERS, 1993, 34 (01) :153-156
[4]   SUPPRESSION OF ALKENE ISOMERIZATION IN PRODUCTS FROM INTRAMOLECULAR HECK REACTIONS BY ADDITION OF TL(I) SALTS [J].
GRIGG, R ;
LOGANATHAN, V ;
SANTHAKUMAR, V ;
SRIDHARAN, V ;
TEASDALE, A .
TETRAHEDRON LETTERS, 1991, 32 (05) :687-690
[5]   PALLADIUM CATALYZED CASCADE CYCLIZATION-CARBONYLATION PROCESSES - RATE ENHANCEMENT BY TL(I) SALTS [J].
GRIGG, R ;
KENNEWELL, P ;
TEASDALE, AJ .
TETRAHEDRON LETTERS, 1992, 33 (50) :7789-7792
[6]   SPIROCYCLES VIA PALLADIUM-CATALYZED CASCADE CYCLIZATION-CARBONYLATION-ANION CAPTURE PROCESSES [J].
GRIGG, R ;
SRIDHARAN, V .
TETRAHEDRON LETTERS, 1993, 34 (46) :7471-7474
[7]   THE SYNTHESIS OF BRIDGED-RING CARBOCYCLES AND HETEROCYCLES VIA PALLADIUM CATALYZED REGIOSPECIFIC CYCLIZATION REACTIONS [J].
GRIGG, R ;
SANTHAKUMAR, V ;
SRIDHARAN, V ;
STEVENSON, P ;
TEASDALE, A ;
THORNTONPETT, M ;
WORAKUN, T .
TETRAHEDRON, 1991, 47 (46) :9703-9720
[8]   NICKEL-PROMOTED INTRAMOLECULAR CYCLIZATION OF VINYL BROMIDES WITH ALKENES AND ALKYNES [J].
LLEBARIA, A ;
CAMPS, F ;
MORETO, J .
TETRAHEDRON LETTERS, 1992, 33 (25) :3683-3686
[9]   THE [NI(CO)4]-PROMOTED CARBONYLATIVE CYCLOADDITION OF ALKYNES AND ALLYL HALIDES FOR THE SYNTHESIS OF 2-CYCLOPENTENONE DERIVATIVES [J].
LLEBARIA, A ;
MORETO, JM .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 451 (1-2) :1-13
[10]   STUDIES ON THE COMPETITIVE NICKEL-PROMOTED CARBONYLATIVE INTRAMOLECULAR CYCLIZATION OF VINYL AND ARYL HALIDES WITH HYDROXYALKENES [J].
LLEBARIA, A ;
DELGADO, A ;
CAMPS, F ;
MORETO, JM .
ORGANOMETALLICS, 1993, 12 (07) :2825-2831