STEREOELECTRONIC FACTORS IN THE SYNTHESIS OF TETRAHYDROFURANS BY HYDROXYL PARTICIPATION IN PHENYLTHIO MIGRATION

被引:25
作者
MCINTYRE, S [1 ]
WARREN, S [1 ]
机构
[1] UNIV CAMBRIDGE,LENSFIELD RD,CAMBRIDGE CB2 1EW,ENGLAND
关键词
D O I
10.1016/S0040-4039(00)97421-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The factors controlling the title reaction were investigated with two tethered hydroxyl nucleophiles and include preferential attack at the more highly substituted carbon atom, preferential formation of the more highly substituted five-membered ring, and preferential closure in the 5-exo-tet sense according to Baldwin's rules. © 1990.
引用
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页码:3457 / 3460
页数:4
相关论文
共 19 条
[1]   PHENYLTHIO(PHS) MIGRATION IN THE STEREOCONTROLLED SYNTHESIS OF ALLYLIC ALCOHOLS WITH 1,4 RELATED CHIRAL CENTERS [J].
AGGARWAL, VK ;
WARREN, S .
TETRAHEDRON LETTERS, 1986, 27 (01) :101-104
[2]   SYNTHESIS OF COMPOUNDS WITH 1,4-RELATED CHIRAL CENTERS BY PHENYLTHIO MIGRATION - SYN AND ANTI-E-2,4-DIMETHYLHEX-3-ENE-1,5-DIOL [J].
AGGARWAL, VK ;
WARREN, S .
TETRAHEDRON LETTERS, 1987, 28 (17) :1925-1928
[3]   STEREOCHEMICAL CONTROL IN THE SYNTHESIS OF TETRAHYDROFURANS BY CYCLIZATION OF DIOLS WITH PHENYLTHIO MIGRATION [J].
AGGARWAL, VK ;
COLDHAM, I ;
MCINTYRE, S ;
SANSBURY, FH ;
VILLA, MJ ;
WARREN, S .
TETRAHEDRON LETTERS, 1988, 29 (38) :4885-4888
[4]   RULES FOR RING-CLOSURE [J].
BALDWIN, JE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736
[5]   RULES FOR RING-CLOSURE - STEREOELECTRONIC CONTROL IN ENDOCYCLIC ALKYLATION OF KETONE ENOLATES [J].
BALDWIN, JE ;
KRUSE, LI .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (07) :233-235
[6]   STEREOCHEMICALLY CONTROLLED SYNTHESIS OF SPIROCYCLIC LACTONES AND ETHERS FROM N-METHYL-4-PIPERIDONE AND 3-QUINUCLIDINONE BY PHENYLTHIO MIGRATION [J].
COLDHAM, I ;
COLLINGTON, EW ;
HALLETT, P ;
WARREN, S .
TETRAHEDRON LETTERS, 1988, 29 (41) :5321-5324
[7]  
DEGROOT A, 1985, SYNTHESIS-STUTTGART, P434
[8]   A NOVEL SYNTHESIS OF ALPHA-SULFENYLATED ALDEHYDES [J].
DEGROOT, A ;
JANSEN, BJM .
TETRAHEDRON LETTERS, 1981, 22 (09) :887-888
[9]   NUCLEOPHILIC-SUBSTITUTION WITH INVERSION OF CONFIGURATION AT THE NUCLEOPHILE [J].
HEATHCOCK, CH ;
VONGELDERN, TW ;
LEBRILLA, CB ;
MAIER, WF .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (07) :968-972
[10]  
HEATHCOCK CH, 1984, ASYMMETRIC SYNTHESIS, V3, P111