2ND-GENERATION AUXILIARY FOR THE ASYMMETRIC ADDITION OF METALATED TETRAHYDROISOQUINOLINES TO ALDEHYDES

被引：19

作者：

ZHANG, PS ^{[1
]}

GAWLEY, RE ^{[1
]}

机构：

[1] UNIV MIAMI,DEPT CHEM,CORAL GABLES,FL 33124

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 21期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)79567-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The selectivity of asymmetric addition of tetrahydroisoquinolyloxazoline Grignard reagents to aldehydes has now been improved to 78-82% ds through the use of a camphor-derived auxiliary. The new auxiliary has broad applicability, with overall yields of chemically and diastereomerically pure addition products now in the 50-58% range.

引用

收藏

页码：2945 / 2948

页数：4

相关论文

共 20 条

[11] MACROMODEL - AN INTEGRATED SOFTWARE SYSTEM FOR MODELING ORGANIC AND BIOORGANIC MOLECULES USING MOLECULAR MECHANICS [J].

MOHAMADI, F ;

RICHARDS, NGJ ;

GUIDA, WC ;

LISKAMP, R ;

LIPTON, M ;

CAUFIELD, C ;

CHANG, G ;

HENDRICKSON, T ;

STILL, WC .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (04) :440-467

[12] CHIRAL DIPOLE-STABILIZED ANIONS - EXPERIMENT AND THEORY IN BENZYLIC AND ALLYLIC SYSTEMS - STEREOSELECTIVE DEPROTONATIONS, PYRAMIDAL INVERSIONS, AND STEREOSELECTIVE ALKYLATIONS OF LITHIATED (TETRAHYDROISOQUINOLYL)OXAZOLINES [J].

REIN, K ;

GOICOECHEAPAPPAS, M ;

ANKLEKAR, TV ;

HART, GC ;

SMITH, GA ;

GAWLEY, RE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (06) :2211-2217

[13] SYNTHESIS OF (-)-EGENINE (DECUMBENSINE) BY ASYMMETRIC CARBONYL ADDITION [J].

REIN, KS ;

GAWLEY, RE .

TETRAHEDRON LETTERS, 1990, 31 (26) :3711-3714

[14] ANALYSIS OF (ALPHA-HYDROXYBENZYL)TETRAHYDROISOQUINOLINE STEREOISOMERS BY PIRKLE COLUMN HPLC - CORRELATION OF ABSOLUTE-CONFIGURATION WITH ORDER OF ELUTION [J].

REIN, KS ;

GAWLEY, RE .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :839-841

[15] SINGLE ELECTRON-TRANSFER IN THE ADDITION OF CHIRAL DIPOLE-STABILIZED ORGANOLITHIUMS TO CARBONYLS - STEREOCHEMISTRY OF A CHIRAL NUCLEOPHILE AS A MECHANISTIC PROBE [J].

REIN, KS ;

CHEN, ZH ;

PERUMAL, PT ;

ECHEGOYEN, L ;

GAWLEY, RE .

TETRAHEDRON LETTERS, 1991, 32 (17) :1941-1944

[16] SYNTHESIS OF THE PHTHALIDE ISOQUINOLINE ALKALOIDS (-)-EGENINE, (-)-CORYTENSINE, AND (-)-BICUCULLINE BY ASYMMETRIC CARBONYL ADDITION OF CHIRAL DIPOLE-STABILIZED ORGANOMETALLICS [J].

REIN, KS ;

GAWLEY, RE .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1564-1569

[17] ON THE STERIC COURSE OF ADDITION OF 1-LITHO-2-PIVALOYL-1,2,3,4-TETRAHYDROISOQUINOLINE AND 1-MAGNESIO-2-PIVALOYL-1,2,3,4-TETRAHYDROISOQUINOLINE TO ALDEHYDES AND KETONES - AN X-RAY CRYSTAL-STRUCTURE DETERMINATION OF THE ORGANOMAGNESIUM REAGENT [J].

SEEBACH, D ;

HANSEN, J ;

SEILER, P ;

GROMEK, JM .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 285 (1-3) :1-13

[18]

SEEBACH D, 1985, CHIMIA, V39, P233

[19] DIASTEREOSELECTIVE HYDROXYALKYLATIONS IN POSITION-1 OF TETRAHYDROISOQUINOLINES AND SYNTHESIS OF APORPHINE, PROTOBERBERINE, AND PHTHALIDE ALKALOIDS [J].

SEEBACH, D ;

HUBER, IMP ;

SYFRIG, MA .

HELVETICA CHIMICA ACTA, 1987, 70 (05) :1357-1379

[20]

SEEBACH D, 1984, ANGEW CHEM INT EDIT, V70, P1944