SYN-ANTI ISOMERISM IN THE REACTIONS OF CIS-3,4-DISUBSTITUTED CYCLOBUTENES .6. CIS-DIHYDROXYLATION WITH OSO4

被引：16

作者：

BURDISSO, M

GANDOLFI, R

RASTELLI, A

机构：

[1] UNIV PAVIA,DIPARTMENTO CHIM ORGAN,V TARAMELLI 10,I-27100 PAVIA,ITALY

[2] UNIV MODENA,DIPARTMENTO CHIM,I-41100 MODENA,ITALY

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 23期

关键词：

D O I：

10.1016/S0040-4039(00)78812-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 1 with OsO4 (carried out in acetone:water=2:1) takes place with moderate to high syn selectivity for X = Cl, OAc, OSO2Me, contrary to the predictions of Kishi's empirical rule but in accordance with the direction of the ground state out-of-plane bending of the olefinic hydrogens of cyclobutenes. Moreover, face selectivity observed is solvent dependent: a decrease in the syn:anti ratio was observed upon replacing methanol for water.

引用

页码：2659 / 2662

页数：4

共 28 条

[21] MODEL-CALCULATIONS OF CHEMICAL INTERACTIONS .2. INTRAMOLECULAR INTERACTIONS AND DOUBLE-BOND PYRAMIDALIZATION IN POLYCYCLIC ALKENES
RASTELLI, A
COCCHI, M
SCHIATTI, E
GANDOLFI, R
BURDISSO, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1990, 86 (05): : 783 - 787
[22] SYN-ANTI ISOMERISM IN THE 1,3-DIPOLAR CYCLOADDITION TO CIS-3,4-DISUBSTITUTED CYCLOBUTENES .4. INTRAMOLECULAR INTERACTIONS
RASTELLI, A
BURDISSO, M
GANDOLFI, R
[J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1990, 3 (03) : 159 - 173
[23] CHROMYL CHLORIDE OXIDATIONS OF OLEFINS - POSSIBLE ROLE OF ORGANOMETALLIC INTERMEDIATES IN OXIDATIONS OF OLEFINS BY OXO TRANSITION-METAL SPECIES
SHARPLESS, KB
TERANISHI, AY
BACKVALL, JE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (09) : 3120 - 3128
[24] ASYMMETRIC OXIDATION OF OLEFINS TO VICINAL DIOLS WITH OSMIUM-TETROXIDE
TOKLES, M
SNYDER, JK
[J]. TETRAHEDRON LETTERS, 1986, 27 (34) : 3951 - 3954
[25] A TRANSITION-METAL-CONTROLLED SYNTHESIS OF (+/-)-ARISTEROMYCIN AND (+/-)-2',3'-DIEPI-ARISTEROMYCIN - AN UNUSUAL DIRECTIVE EFFECT IN HYDROXYLATIONS
TROST, BM
KUO, GH
BENNECHE, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) : 621 - 622
[26] AN EVALUATION OF SIGMA-SIGMA-STAR AND TORSIONAL EFFECTS IN THE OSMYLATION AND EPOXIDATION OF 4-TERT-BUTYLMETHYLENECYCLOHEXANE DERIVATIVES
VEDEJS, E
DENT, WH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) : 6861 - 6862
[27] HYPERCONJUGATIVE EFFECTS OF ALLYLIC SUBSTITUENTS ARE NOT IMPORTANT IN OSMYLATIONS
VEDEJS, E
MCCLURE, CK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (05) : 1094 - 1096
[28] THEORETICAL EVIDENCE IN SUPPORT OF THE ANH-EISENSTEIN ELECTRONIC MODEL IN CONTROLLING PI-FACIAL STEREOSELECTIVITY IN NUCLEOPHILIC ADDITIONS TO CARBONYL-COMPOUNDS
WONG, SS
PADDONROW, MN
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (06) : 456 - 458

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