CHELATION AND NONCHELATION CONTROLLED STEREOSELECTIVE REDUCTION OF ALPHA-METHOXY-ALPHA-PHENYLTHIO KETONES

被引：10

作者：

ANNUNZIATA, R ^{[1
]}

CINQUINI, M ^{[1
]}

COZZI, F ^{[1
]}

FUCHICELLO, A ^{[1
]}

机构：

[1] UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY

来源：

TETRAHEDRON | 1991年 / 47卷 / 23期

关键词：

D O I：

10.1016/S0040-4020(01)80909-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of a-methoxy-a-phenylthio substituted ketones bearing an additional stereocenter in a1-position was prepared, and the reduction with chelating and non chelating reagents was studied. ''Internal matched'' pairs (leading to highly stereoselective processes) and ''mismatched'' pairs were identified, and possible transition structures were suggested.

引用

页码：3853 / 3868

页数：16

共 28 条

[1]

Anh N. T., 1980, TOP CURR CHEM, V88, P145

[2] STEREOSELECTIVE SYNTHESIS OF (E)-2-ALKENE-1,4-DIOLS VIA METALATED ALLYLIC SULFOXIDES [J].

ANNUNZIATA, R ;

CINQUINI, M ;

COZZI, F ;

RAIMONDI, L ;

STEFANELLI, S .

TETRAHEDRON, 1986, 42 (19) :5443-5450

[3] THE STABILIZATION OF ALPHA-SUBSTITUTED OXYCARBANIONS AND THIOCARBANIONS [J].

BERNARDI, F ;

BOTTONI, A ;

VENTURINI, A ;

MANGINI, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (26) :8171-8175

[4] REDUCTIVE LITHIATION MEDIATED ANIONIC CYCLIZATIONS AND [2,3]-SIGMATROPIC REARRANGEMENTS [J].

BROKA, CA ;

SHEN, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) :2981-2984

[5]

CHA JK, 1984, TETRAHEDRON, V40, P2255

[6]

ELIEL EL, 1983, ASYMMETRIC SYNTHESIS, V2, P125

[7] ASYMMETRIC-SYNTHESIS BASED ON 1,3-OXATHIANES .4. MECHANISM OF ASYMMETRIC INDUCTION IN THE REACTIONS OF OXATHIANYL KETONES [J].

FRYE, SV ;

ELIEL, EL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) :484-489

[8]

GENSLER WJ, 1960, J AM CHEM SOC, V82, P60

[9]

GRAUERT M, 1985, LIEBIGS ANN CHEM, P1817

[10] ENANTIOSPECIFIC SYNTHESIS OF PROTECTED 4-DEOXY-L-THREOSE AND 4-DEOXY-L-ERYTHROSE VIA DIASTEREOSELECTIVE REDUCTION OF L-LACTIC ACID-DERIVED KETONES [J].

GUANTI, G ;

BANFI, L ;

NARISANO, E .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (02) :136-138

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