STEREOSELECTIVE EPOXIDATIONS AND ELECTROPHILIC ADDITIONS TO PARTIAL ERGOT ALKALOIDS AND CONFORMATIONALLY-FIXED STYRENES - EXPERIMENTAL AND THEORETICAL MODELING EVIDENCE FOR THE IMPORTANCE OF TORSIONAL STEERING AS A STEREOCONTROL ELEMENT

被引：40

作者：

MARTINELLI, MJ ^{[1
]}

PETERSON, BC ^{[1
]}

KHAU, VV ^{[1
]}

HUTCHISON, DR ^{[1
]}

LEANNA, MR ^{[1
]}

AUDIA, JE ^{[1
]}

DROSTE, JJ ^{[1
]}

WU, YD ^{[1
]}

HOUK, KN ^{[1
]}

机构：

[1] UNIV CALIF LOS ANGELES,DEPT CHEM & BIOCHEM,LOS ANGELES,CA 90024

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 08期

关键词：

D O I：

10.1021/jo00087a042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Partial ergot alkaloid substrates and related conformationally-fixed styrenes undergo epoxidation, osmium tetraoxide dihydroxylation, and hydrobromination with a level of stereoselectivity which cannot be explained by steric control but is consistent with electrophilic attack to minimize torsional strain. Force-field modeling is consistent with the importance of torsional steering as the dominant stereochemical control element.

引用

页码：2204 / 2210

页数：7

共 41 条

[1] CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].

ALLINGER, NL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8127-8134

[2] TRANSITION STRUCTURE FOR THE EPOXIDATION OF ALKENES WITH PEROXY ACIDS - A THEORETICAL-STUDY [J].

BACH, RD ;

OWENSBY, AL ;

GONZALEZ, C ;

SCHLEGEL, HB ;

MCDOUALL, JJW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) :2338-2339

[3] PREPARATION AND STEREOCHEMICAL CHARACTERIZATION OF DIASTEREOISOMERIC 1-PHENYL-4-T-BUTYLCYCLOHEXENE OXIDES AND 1-PHENYL-4-T-BUTYLCYCLOHEXANE-1,2-DIOLS [J].

BERTI, G ;

MACCHIA, B ;

MACCHIA, F .

TETRAHEDRON, 1968, 24 (04) :1755-&

[4]

Berti G., 1973, TOP STEREOCHEM, V7, P93

[5]

BURKERT U, 1980, MOL MECHANICS

[6]

CEDHEIM L, 1973, SYNTHESIS-STUTTGART, P159

[7]

CHEREST M, 1968, TETRAHEDRON LETT, P2205

[8]

CHEREST M, 1968, TETRAHEDRON LETT, P2201

[9] REVERSAL OF PI-FACIAL DIASTEREOSELECTION UPON ELECTRONEGATIVE SUBSTITUTION OF THE SUBSTRATE AND THE REAGENT [J].

CIEPLAK, AS ;

TAIT, BD ;

JOHNSON, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (22) :8447-8462

[10]

EVANS DA, 1984, ASYMMETRIC SYNTHESIS, V3, P1

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