STUDIES TOWARD A MODEL FOR PREDICTING THE DIASTEREOSELECTIVITY IN THE ELECTROPHILIC AMINATION OF CHIRAL 1,3,2-OXAZAPHOSPHOLANES

被引：19

作者：

JOMMI, G

MIGLIERINI, G

PAGLIARIN, R

SELLO, G

SISTI, M

机构：

[1] Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, 20133 Milano

来源：

TETRAHEDRON | 1992年 / 48卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(01)88266-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A model. has been developed for predicting the diastereoselectivity in the electrophilic amination of chiral 1,3,2-oxazaphospholanes derived from ephedrine and pseudoephedrine derivatives. The influence of the five-membered ring conformations and of the bulkiness of the ring substituents has been deeply analyzed both for reactivity prediction and for H-1-NMR data interpretation. The theoretical and experimental results are in good agreement.

引用

收藏

页码：7275 / 7288

页数：14

相关论文

共 21 条

[1] NEW CHIRAL LIGAND FOR THE ASYMMETRIC CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS TO ENONES [J].

ALEXAKIS, A ;

MUTTI, S ;

NORMANT, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6332-6334

[2] NOREPHEDRINE-DERIVED 2-ALKENYLOXAZOLIDINES - STEREOCHEMISTRY OF CYCLIZATION AND ALLYLIC STEREOCENTER DIRECTED ASYMMETRIC CONJUGATE ADDITION [J].

BERNARDI, A ;

CARDANI, S ;

PILATI, T ;

POLI, G ;

SCOLASTICO, C ;

VILLA, R .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1600-1607

[3] 1,3,2-OXAZAPHOSPHOLIDINES FROM (-)-EPHEDRINE - INTERMEDIATES FOR STEREOSPECIFIC SYNTHESIS OF OPTICALLY-ACTIVE DIALKYL ALKYLPHOSPHONOTHIOATES AND DIALKYL ALKYLPHOSPHONO-SELENOATES, TRIALKYL PHOSPHORO-THIOATES AND TRIALKYL PHOSPHONO-SELENOATES, DIALKYL METHYLPHOSPHONATES, AND TRIALKYL PHOSPHATES [J].

COOPER, DB ;

HALL, CR ;

HARRISON, JM ;

INCH, TD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (17) :1969-1980

[4] ASYMMETRIC ELECTROPHILIC AMINATION OF CHIRAL PHOSPHORUS-STABILIZED ANIONS [J].

DENMARK, SE ;

CHATANI, N ;

PANSARE, SV .

TETRAHEDRON, 1992, 48 (11) :2191-2208

[5] CONFIGURATION, CONFORMATION, AND COLLIGATIVE PROPERTIES OF A PHOSPHORUS-STABILIZED ANION [J].

DENMARK, SE ;

MILLER, PC ;

WILSON, SR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) :1468-1470

[6] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].

DEWAR, MJS ;

ZOEBISCH, EG ;

HEALY, EF ;

STEWART, JJP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909

[7] THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO AND ALPHA-HYDRAZINO ACID-DERIVATIVES VIA THE STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES WITH AZODICARBOXYLATE ESTERS [J].

EVANS, DA ;

BRITTON, TC ;

DOROW, RL ;

DELLARIA, JF .

TETRAHEDRON, 1988, 44 (17) :5525-5540

[8] STUDIES OF SPECIFICALLY SUBSTITUTED ORGANOPHOSPHORUS DERIVATIVES .4. CONCERNING ANGULAR DEPENDENCE OF VICINAL P-31-H-1 COUPLING-CONSTANTS OF PHOSPHONATE AND OF HYDROXYPHOSPHONATE DERIVATIVES [J].

EVELYN, L ;

HALL, LD ;

STEINER, PR ;

STOKES, DH .

ORGANIC MAGNETIC RESONANCE, 1973, 5 (03) :141-145

[9] ASYMMETRIC-SYNTHESIS OF DIETHYL ALPHA-AMINO-ALPHA-ALKYL-PHOSPHONATES BY ALKYLATION OF THE CHIRAL SCHIFF-BASE DERIVED FROM (+)-KETOPINIC ACID AND DIETHYLAMINOMETHYL PHOSPHONATE [J].

FERRARI, M ;

JOMMI, G ;

MIGLIERINI, G ;

PAGLIARIN, R ;

SISTI, M .

SYNTHETIC COMMUNICATIONS, 1992, 22 (01) :107-123

[10] THE RELATIONSHIP BETWEEN PROTON-PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .1. AN EMPIRICAL GENERALIZATION OF THE KARPLUS EQUATION [J].

HAASNOOT, CAG ;

DELEEUW, FAAM ;

ALTONA, C .

TETRAHEDRON, 1980, 36 (19) :2783-2792