ASYMMETRIC ADDITIONS TO DICHLOROPHENYLDIOXANE - A NEW CHIRAL ACETAL

被引：11

作者：

ANDRUS, MB

LEPORE, SD

机构：

[1] Purdue University, Department of Chemistry, 1393 Brown Laboratories. West Lafayette

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 50期

关键词：

D O I：

10.1016/0040-4039(95)01960-P

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-(2,6-Dichlorophenyl)-1,3-dioxanes have been reacted with weak nucleophiles and TiCl4 to give benzyl ethers with high selectivity. The major products are consistent with an S(N)2-like mechanism. The benzyl ether is removed in one step using Li/NH3 to give non-racemic secondary alcohols.

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页码：9149 / 9152

页数：4

相关论文

共 21 条

[1] CHIRAL ACETALS IN ASYMMETRIC-SYNTHESIS [J].

ALEXAKIS, A ;

MANGENEY, P .

TETRAHEDRON-ASYMMETRY, 1990, 1 (08) :477-511

[2] CHIRAL ACETALS IN ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SUBSTITUTION OR ELIMINATION-REACTIONS [J].

ALEXAKIS, A ;

MANGENEY, P ;

GHRIBI, A ;

MAREK, I ;

SEDRANI, R ;

GUIR, C ;

NORMANT, J .

PURE AND APPLIED CHEMISTRY, 1988, 60 (01) :49-56

[3]

ALLINGER NL, 1966, J ORG CHEM, V31, P804

[4] ASYMMETRIC-SYNTHESIS VIA ACETAL TEMPLATES .3. ON THE STEREOCHEMISTRY OBSERVED IN THE CYCLIZATION OF CHIRAL ACETALS OF POLYOLEFINIC ALDEHYDES - FORMATION OF OPTICALLY-ACTIVE HOMOALLYLIC ALCOHOLS [J].

BARTLETT, PA ;

JOHNSON, WS ;

ELLIOTT, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (07) :2088-2089

[5] CONFORMATIONAL-ANALYSIS OF CHIRAL ALKENES AND OXONIUM IONS - ABINITIO MOLECULAR-ORBITAL CALCULATIONS AND AN IMPROVED MM2 FORCE-FIELD [J].

BROEKER, JL ;

HOFFMANN, RW ;

HOUK, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) :5006-5017

[6] CHIRAL SYNTHESIS VIA ORGANOBORANES .7. DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF ERYTHRO-BETA-METHYLOMOALLYL AND THREO-BETA-METHYLHOMOALLYL ALCHOLS VIA ENANTIOMERIC (Z)-CROTYLBORANE AND (E)-CROTYLBORANE [J].

BROWN, HC ;

BHAT, KS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :5919-5923

[7] ASYMMETRIC-SYNTHESIS VIA CHIRAL ACETAL TEMPLATES .7. FURTHER-STUDIES ON THE CYANATION REACTION - THE USE OF ACETALS DERIVED FROM DIOLS WITH ONE CHIRAL CENTER [J].

CHOI, VMF ;

ELLIOTT, JD ;

JOHNSON, WS .

TETRAHEDRON LETTERS, 1984, 25 (06) :591-594

[8]

DALE JA, 1969, J AM CHEM SOC, V90, P3732

[9] STUDIES ON THE MECHANISM AND ORIGIN OF STEREOSELECTIVE OPENING OF CHIRAL DIOXANE ACETALS [J].

DENMARK, SE ;

ALMSTEAD, NG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) :8089-8110

[10] CONFORMATIONAL-ANALYSIS .40. CONFORMATION OF 1-METHYL-1-PHENYLCYCLOHEXANE AND THE CONFORMATIONAL ENERGIES OF THE PHENYL AND VINYL GROUPS [J].

ELIEL, EL ;

MANOHARAN, M .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (09) :1959-1962