INTRAMOLECULAR TRAPPING OF DIFLUOROALKYL RADICALS BY TETHERED OLEFINS IN THE ASYMMETRIC-SYNTHESIS OF 2,4-DISUBSTITUTED-3,3-DIFLUOROTETRAHYDROFURANS

被引：20

作者：

CAVICCHIO, G ^{[1
]}

MARCHETTI, V ^{[1
]}

ARNONE, A ^{[1
]}

BRAVO, P ^{[1
]}

VIANI, F ^{[1
]}

机构：

[1] POLITECN MILAN,DIPARTMENTO CHIM,CTR STUDIO SOSTANZE ORGANICHE NAT,CNR,I-20133 MILAN,ITALY

来源：

TETRAHEDRON | 1991年 / 47卷 / 45期

关键词：

INTRAMOLECULAR TRAPPING; DIFLUOROALKYL RADICALS; ASYMMETRIC SYNTHESIS; DIFLUOROTETRAHYDROFURANS;

D O I：

10.1016/S0040-4020(01)80890-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically pure propenyl ethers of 3-sulphenyl-, 3-sulphinyl-, and 3-sulphonyl-1-chloro-1,1-difluoropropan-2-ols were submitted to radical cyclization affording, with moderate to high diastereoselectivity, 3,3-difluorotetrahydrofurans containing in 2 and 4 positions various substituents. Detailed NMR analysis allowed to measure trans/cis ratios and to establish the structure of the products.

引用

页码：9439 / 9448

页数：10

共 32 条

[1]

ARNONE A, IN PRESS J CHEM S P1

[2] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[3]

Banks R. E., 1979, ORGANOFLUORINE CHEM

[4] HOMOCHIRAL ALPHA-FLUOROKETONES FROM RACEMIC ALPHA-FLUOROCARBOXYLIC ESTERS AND ENANTIOMERICALLY PURE SULFOXIDES [J].

BRAVO, P ;

RESNATI, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (03) :218-219

[5]

BRAVO P, 1990, GAZZ CHIM ITAL, V120, P275

[6]

BRAVO P, 1989, GAZZ CHIM ITAL, V119, P323

[7]

BRAVO P, 1988, SYNTHESIS-STUTTGART, P955

[8]

BRAVO P, 1986, SYNTHESIS-STUTTGART, P579

[9] PREPARATION AND PROPERTIES OF CHIRAL FLUOROORGANIC COMPOUNDS [J].

BRAVO, P ;

RESNATI, G .

TETRAHEDRON-ASYMMETRY, 1990, 1 (10) :661-692

[10]

BRAVO P, 1989, J FLUORINE CHEM, V45, P119

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