ELECTROSTATIC EFFECTS IN 1,3-DIPOLAR CYCLOADDITION REACTIONS TO CHIRAL ALLYL ETHERS - A RATIONALE FOR THE EXPERIMENTALLY OBSERVED DIASTEREOSELECTIVITIES

被引：42

作者：

ANNUNZIATA, R

BENAGLIA, M

CINQUINI, M

RAIMONDI, L

机构：

[1] UNIV MILAN,CTR CNR,VIA CAMILLO GOLGI 19,I-20133 MILAN,ITALY

[2] UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY

来源：

TETRAHEDRON | 1993年 / 49卷 / 38期

关键词：

D O I：

10.1016/S0040-4020(01)96268-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Semiempirical (PM3) and ab initio (RHF/3-21G) transition structures for 1,3-dipolar cycloadditions of 5 different dipoles to alkenes were analyzed; the differences in 1,3-dipole charge distribution offer a rationale for the different stereoselectivities experimentally observed in the reactions with chiral allyl ethers.

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页码：8629 / 8636

页数：8

相关论文

共 33 条

[1]

ANNUNZIATA R, 1989, GAZZ CHIM ITAL, V119, P253

[2] 1,3-DIPOLAR CYCLOADDITION REACTIONS OF AZOMETHINE YLIDES ON ENANTIOMERICALLY PURE (E)-GAMMA-ALKOXY-ALPHA,BETA-UNSATURATED ESTERS [J].

ANNUNZIATA, R ;

CINQUINI, M ;

COZZI, F ;

RAIMONDI, L ;

PILATI, T .

TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1329-1342

[3] THE DIASTEREOSELECTIVITY OF INTERMOLECULAR NITRONE CYCLOADDITION TO CHIRAL ALLYL DERIVATIVES [J].

ANNUNZIATA, R ;

CINQUINI, M ;

COZZI, F ;

GIARONI, P ;

RAIMONDI, L .

TETRAHEDRON LETTERS, 1991, 32 (13) :1659-1662

[4]

[Anonymous], 1986, AB INITIO MOL ORBITA

[5] DETERMINING ATOM-CENTERED MONOPOLES FROM MOLECULAR ELECTROSTATIC POTENTIALS - THE NEED FOR HIGH SAMPLING DENSITY IN FORMAMIDE CONFORMATIONAL-ANALYSIS [J].

BRENEMAN, CM ;

WIBERG, KB .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (03) :361-373

[6] A THEORETICAL-STUDY OF INTRAMOLECULAR DIELS-ALDER AND 1,3-DIPOLAR CYCLOADDITION STEREOSELECTIVITY USING ABINITIO METHODS, SEMIEMPIRICAL METHODS, AND A TANDEM QUANTUM MECHANIC MOLECULAR MECHANIC METHOD [J].

BROWN, FK ;

SINGH, UC ;

KOLLMAN, PA ;

RAIMONDI, L ;

HOUK, KN ;

BOCK, CW .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (18) :4862-4869

[7] THE STO-3G TRANSITION STRUCTURE OF THE DIELS-ALDER REACTION [J].

BROWN, FK ;

HOUK, KN .

TETRAHEDRON LETTERS, 1984, 25 (41) :4609-4612

[8] A FORCE-FIELD MODEL FOR THE TRANSITION STRUCTURES OF INTRAMOLECULAR NITRILE OXIDE CYCLOADDITIONS [J].

BROWN, FK ;

RAIMONDI, L ;

WU, YD ;

HOUK, KN .

TETRAHEDRON LETTERS, 1992, 33 (31) :4405-4408

[9]

BROWN FK, 1985, THESIS U PITTSBURGH

[10] ATOMIC CHARGES DERIVED FROM ELECTROSTATIC POTENTIALS - A DETAILED STUDY [J].

CHIRLIAN, LE ;

FRANCL, MM .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1987, 8 (06) :894-905

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