STEREOELECTRONIC CONTROL IN THE REDUCTIVE OPENING OF CYCLOPROPYLOGOUS ALPHA-HALOKETONES

被引：15

作者：

BEERLI, R ^{[1
]}

BRUNNER, EJ ^{[1
]}

BORSCHBERG, HJ ^{[1
]}

机构：

[1] SWISS FED INST TECHNOL,ORGAN CHEM LAB,UNIV STR 16,CH-8092 ZURICH,SWITZERLAND

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 43期

关键词：

D O I：

10.1016/S0040-4039(00)79012-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Each of the two epimeric cyclopropylogous alpha-bromoketones 4 and 5 could be cleaved reductively with high diastereoselectivity to either (E)- or (Z)- 2,2-dimethyl-5-(l-propenyl)cyclohexanone (6 or 7, resp.), depending on the reducing agent employed (SmI2 Or NaHTe). Thus, it was demonstrated that both reducing systems bring across the stereochemical information contained in the starting materials, albeit in an opposing and, therefore, complementary sense.

引用

页码：6449 / 6452

页数：4

共 24 条

[1] ORGANIC QUANTUM CHEMISTRY .13. ELECTRONIC SPECTRA OF ALPHA-HALO KETONES [J].

ALLINGER, NL ;

TAI, JC ;

MILLER, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (19) :4495-&

[2] SAMARIUM DIIODIDE - A USEFUL ELECTRON-DONOR IN ORGANIC-SYNTHESIS [J].

ANANTHANARAYAN, TP ;

GALLAGHER, T ;

MAGNUS, P .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (12) :709-710

[3] NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].

BARTON, DHR ;

MCCOMBIE, SW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585

[4] INVESTIGATIONS CONCERNING AN UNEXPECTED REACTION BETWEEN THE DIMSYL ANION (= (METHYLSULFINYL)METHANIDE) AND A GAMMA,DELTA-EPOXY-KETONE [J].

BEERLI, R ;

BORSCHBERG, HJ .

HELVETICA CHIMICA ACTA, 1992, 75 (01) :190-202

[5]

BEERLI R, UNPUB

[6] REACTIONS INVOLVING ELECTRON TRANSFER .1. REDUCTION OF 2,2,6,6-TETRAMETHYL-4-HEPTEN/3-ONE [J].

BOWERS, KW ;

GIESE, RW ;

GRIMSHAW, J ;

HOUSE, HO ;

KOLODNY, NH ;

KRONBERG.K ;

ROE, DK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (09) :2783-&

[7]

BRUNNER EJ, 1987, THESIS ETH ZURICH

[8] DEHALOGENATION OF ALPHA-CHLORO AND ALPHA-BROMO KETONES - USE OF SODIUM O,O-DIETHYL PHOSPHOROTELLUROATE [J].

CLIVE, DLJ ;

BEAULIEU, PL .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (06) :1124-1126

[9]

Deslongchamps P., 1983, STEREOELECTRONIC EFF

[10] DIVALENT LANTHANIDE DERIVATIVES IN ORGANIC-SYNTHESIS .1. MILD PREPARATION OF SMI2 AND YBI2 AND THEIR USE AS REDUCING OR COUPLING AGENTS [J].

GIRARD, P ;

NAMY, JL ;

KAGAN, HB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (08) :2693-2698

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