A NOVEL CHIRAL AUXILIARY FROM CHIRAL SPIRANES - CIS,CIS-(+) AND (-)-SPIRO[4.4]NONANE-1,6-DIOL AS CHIRAL MODIFIER IN LITHIUM ALUMINUM-HYDRIDE REDUCTION OF PHENYL ALKYL KETONES

被引：83

作者：

SRIVASTAVA, N ^{[1
]}

MITAL, A ^{[1
]}

KUMAR, A ^{[1
]}

机构：

[1] CENT DRUG RES INST,DIV PROC DEV,LUCKNOW 226001,UTTAR PRADESH,INDIA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1992年 / 06期

关键词：

D O I：

10.1039/c39920000493

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

LiAlH4 reduction of phenyl alkyl ketones employing the hitherto unexplored chiral auxiliary cis, cis-(+)- and (-)-spiro[4.4]nonane-1,6-diol as chiral modifier gives the corresponding alcohol in 85-90% e.e. (enantiomeric excess).

引用

页码：493 / 494

页数：2

共 16 条

[1] RECENT ADVANCES IN ASYMMETRIC-SYNTHESIS .2. [J].

APSIMON, JW ;

COLLIER, TL .

TETRAHEDRON, 1986, 42 (19) :5157-5254

[2] SELECTIVE REDUCTIONS .40. A CRITICAL-EXAMINATION OF THE RELATIVE EFFECTIVENESS OF VARIOUS REDUCING AGENTS FOR THE ASYMMETRIC REDUCTION OF DIFFERENT CLASSES OF KETONES [J].

BROWN, HC ;

PARK, WS ;

CHO, BT ;

RAMACHANDRAN, PV .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24) :5406-5412

[3] SYNTHESIS OF OPTICALLY-ACTIVE COMPOUNDS - A LARGE-SCALE PERSPECTIVE [J].

CROSBY, J .

TETRAHEDRON, 1991, 47 (27) :4789-4846

[4] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[5] CHIRALITY OF ENANTIOMERIC SPIRO[4,4]NONAN-1,6-DIONES [J].

GERLACH, H .

HELVETICA CHIMICA ACTA, 1968, 51 (07) :1587-&

[6]

GRANDBOIS ER, 1983, ASYMMETRIC SYNTHESIS, V2, pCH3

[7] RELATIVE CONFIGURATIONS OF THE 2 1-KETO-6-HYDROXYSPIRO[4.4]NONANES AND THE 3 1,6-DIHYDROXYSPIRO[4.4]NONANES [J].

HARDEGGER, E ;

MAEDER, E ;

SEMARNE, HM ;

CRAM, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (11) :2729-2737

[8]

Morrison J. D., 1983, ASYMMETRIC SYNTHESIS, V1-5

[9]

NARASAKA K, 1991, SYNTHESIS-STUTTGART, V1, P1

[10]

NOGRADI M, 1987, STEREOSELECTIVE SYNT

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