STEREODIVERGENT SYNTHESIS OF OPTICALLY-ACTIVE TERTIARY ALCOHOLS VIA ADDITION-REACTION OF CHIRAL 2-ACYL OXAZOLIDINE WITH ORGANOMETALLICS

被引：40

作者：

UKAJI, Y ^{[1
]}

YAMAMOTO, K ^{[1
]}

FUKUI, M ^{[1
]}

FUJISAWA, T ^{[1
]}

机构：

[1] MIE UNIV, DEPT CHEM MAT, TSU, MIE 514, JAPAN

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 25期

关键词：

D O I：

10.1016/0040-4039(91)80649-Q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It was observed that diastereoselectivity in an addition reaction to chiral 2-acyl oxazolidine, derived from (S)-prolinol, can be fully regulated under appropriate conditions. Addition of organotitanium triisopropoxides provided (S)-tertiary alcohols, while organolithium reagents afforded the corresponding (R)-alcohols. Application of this methodology was demonstrated in the synthesis of (+)- and (-)-trihexyphenidyl.

引用

收藏

页码：2919 / 2922

页数：4

相关论文

共 18 条

[1] AMINOALKYL TERTIARY CARBINOLS AND DERIVED PRODUCTS .4. SPASMOLYTICS - PHENYL-CARBINOLS AND CYCLOHEXYLPHENYL-CARBINOLS [J].

ADAMSON, DW ;

BARRETT, PA ;

WILKINSON, S .

JOURNAL OF THE CHEMICAL SOCIETY, 1951, (JAN) :52-60

[2]

Adamson DW, 1956, GB, Patent No. 750156

[3] NOREPHEDRINE DERIVED 2-METHOXY OXAZOLIDINES AS CHIRAL FORMYL CATION EQUIVALENTS [J].

BERNARDI, A ;

CARDANI, S ;

CARUGO, O ;

COLOMBO, L ;

SCOLASTICO, C ;

VILLA, R .

TETRAHEDRON LETTERS, 1990, 31 (19) :2779-2782

[4]

CLAUSS K, 1968, LIEBIGS ANN CHEM, V711, P19

[5] ANTISPASMODICS .3. STUDY OF THE AMINO GROUP IN THE TERTIARY BETA-AMINO ALCOHOLS [J].

DENTON, JJ ;

NEIER, WB ;

LAWSON, VA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (06) :2053-2054

[6] ANTISPASMODICS .5. TERTIARY ALPHA-AMINO AND GAMMA-AMINO ALCOHOLS AND QUATERNARY SALTS OF BETA-AMINO ALCOHOLS [J].

DENTON, JJ ;

LAWSON, VA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (07) :3279-3281

[7] ASYMMETRIC SYNTHESES BASED ON 1,3-OXATHIANES .1. SCOPE OF THE REACTION [J].

ELIEL, EL ;

MORRISNATSCHKE, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (10) :2937-2942

[8] DIASTEREOFACIAL CONTROL IN THE REACTION OF CHIRAL ALPHA-AMINO KETONES WITH SEVERAL ORGANOMETALLICS [J].

FUJISAWA, T ;

FUNABORA, M ;

UKAJI, Y ;

SATO, T .

CHEMISTRY LETTERS, 1988, (01) :59-62

[9] DIASTEREOFACIAL CONTROLLED ADDITION-REACTION OF ALKOXYMETHYLKETONES MODIFIED BY (2R, 4R)-2,4-PENTANEDIOL WITH ORGANOMETALLICS [J].

FUJISAWA, T ;

WATAI, T ;

SUGIYAMA, T ;

UKAJI, Y .

CHEMISTRY LETTERS, 1989, (11) :2045-2048

[10] EITHER DIASTEREOFACIAL DIFFERENTIATION IN THE REACTION OF CHIRAL THIOMETHYLKETONES WITH APPROPRIATE ORGANOMETALLICS [J].

FUJISAWA, T ;

TAKEMURA, I ;

UKAJI, Y .

TETRAHEDRON LETTERS, 1990, 31 (38) :5479-5482