ELECTRONIC EFFECTS ON PI-FACIAL STEREOSELECTIVITY IN ELECTROPHILIC ADDITIONS TO ALLYLIC BONDS - STEREOSELECTIVE EPOXIDATION OF ALLYLIC FLUORIDES

被引：25

作者：

FUJITA, M

ISHIZUKA, H

OGURA, K

机构：

[1] Department of Applied Chemistry, Faculty of Engineering, Chiba University, Chiba, 260

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 44期

关键词：

D O I：

10.1016/0040-4039(91)80168-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The electronic stabilization of the transition state in electrophilic additions to allylic bonds is discussed through m-CPBA oxidation of allylic fluorides; the stereoselectivity is interpreted by a transition-state model where the most electronegative atom (fluorine) is oriented at the inside position as supported by theoretical examinations.

引用

页码：6355 / 6358

页数：4

共 20 条

[1] ANH NT, 1977, NOUV J CHIM, V1, P61
[2] BINKLEY JS, 437 QCPE PROGR
[3] MODELING CHEMICAL-REACTIVITY .7. THE EFFECT OF A CHANGE IN RATE-LIMITING STEP ON THE STEREOSELECTIVITY OF ELECTROPHILIC ADDITION TO ALLYLIC ALCOHOLS AND RELATED CHIRAL ALKENES
CHAMBERLIN, AR
MULHOLLAND, RL
KAHN, SD
HEHRE, WJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) : 672 - 677
[4] ASYMMETRIC INDUCTION AND [2+1] CYCLOADDITIONS .3. DIASTEREOSELECTIVE EPOXIDATIONS OF SECONDARY ALPHA ETHYLENIC ALCOHOLS AND STEREODIRECTED SYNTHESES OF ALPHA EPOXY ALCOHOLS
CHAUTEMPS, P
PIERRE, JL
[J]. TETRAHEDRON, 1976, 32 (05) : 549 - 557
[5] BROMOFLUORINATION OF ALLYLIC ALCOHOLS BY N-BROMOSUCCINIMIDE AND TRIETHYLAMINE TRIS-HYDROFLUORIDE (NBS/ET3N,3HF), A CONVENIENT ROUTE TO EPIFLUOROHYDRINE
CHEHIDI, I
CHAABOUNI, MM
BAKLOUTI, A
[J]. TETRAHEDRON LETTERS, 1989, 30 (24) : 3167 - 3170
[6] REVERSAL OF PI-FACIAL DIASTEREOSELECTION UPON ELECTRONEGATIVE SUBSTITUTION OF THE SUBSTRATE AND THE REAGENT
CIEPLAK, AS
TAIT, BD
JOHNSON, CR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (22) : 8447 - 8462
[7] CIEPLAK AS, 1981, J AM CHEM SOC, V103, P4540, DOI 10.1021/ja00405a041
[8] NEGATIVE HYPERCONJUGATION DOES NOT PLAY AN IMPORTANT ROLE IN ALPHA-FLUORO SULFIDES - AN EXPERIMENTAL DEMONSTRATION
FUJITA, M
SUZUKI, M
OGATA, K
OGURA, K
[J]. TETRAHEDRON LETTERS, 1991, 32 (11) : 1463 - 1466
[9] Hirsch J. A., 1967, TOPICS STEREOCHEMIST, V1, P199, DOI [10.1002/9780470147108.ch4, DOI 10.1002/9780470147108.CH4]
[10] STERIC MODELS FOR STEREOSELECTIVITY OF NITRILE OXIDE CYCLOADDITIONS TO CHIRAL ALKENES
HOUK, KN
DUH, HY
WU, YD
MOSES, SR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (10) : 2754 - 2755

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