ASYMMETRIC FUNCTIONALIZATION OF BICYCLOALKENES BY CATALYTIC ENANTIOPOSITION-SELECTIVE HYDROSILYLATION

被引：91

作者：

UOZUMI, Y

LEE, SY

HAYASHI, T

机构：

[1] HOKKAIDO UNIV,CATALYSIS RES CTR,SAPPORO,HOKKAIDO 060,JAPAN

[2] HOKKAIDO UNIV,GRAD SCH PHARMACEUT SCI,SAPPORO,HOKKAIDO 060,JAPAN

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 47期

关键词：

D O I：

10.1016/S0040-4039(00)60868-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrosilylation of norbornene with trichlorosilane in the presence of palladium catalyst (0.01-0.1 mol %) coordinated with (R)-MOP ligand gave a quantitative yield of exo-2-trichlorositylnorbornane, which was oxidized with hydrogen peroxide to give (1S,2S,4R)-exo-2-norbornanol in 96% ee. The similar hydrosilylation and oxidation of endo-5,6-dicarbomethoxy-2-norbornene, bicyclo[2.2.2]octene, and norbornadiene gave the corresponding bicyclic alcohols of 94% ee, 92% ee, and 95% ee, respectivery.

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页码：7185 / 7188

页数：4

相关论文

共 46 条

[1] PREPARATION OF METHYL 10-OXO-15S-HYDROXYPROSTA-5E,13Z-DIENOATE [J].

ARNDT, HC ;

RAJANI, C .

TETRAHEDRON LETTERS, 1982, 23 (23) :2365-2368

[2] REACTION OF OPTICALLY-ACTIVE EXO-2-BROMONORBORNANE AND ENDO-2-BROMONORBORNANE WITH NITRONIUM TETRAFLUOROBORATE IN ACETONITRILE - EVIDENCE FOR A CARBENIUM ION PATHWAY [J].

BACH, RD ;

HOLUBKA, JW ;

TAAFFEE, TH .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 44 (01) :35-38

[3] A SIMPLE SYNTHESIS OF A STABLE THROMBOXANE-A2 ANALOG [J].

BARRACLOUGH, P .

TETRAHEDRON LETTERS, 1980, 21 (19) :1897-1900

[4] GENERAL-SYNTHESIS OF CARBANUCLEOSIDES VIA REGIOSPECIFIC EPOXIDE OPENING BY THE AGLYCONE [J].

BAUMGARTNER, H ;

MARSCHNER, C ;

PUCHER, R ;

GRIENGL, H .

TETRAHEDRON LETTERS, 1991, 32 (05) :611-614

[5] HYDROBORATION .61. DIISOPINOCAMPHEYLBORANE OF HIGH OPTICAL PURITY - IMPROVED PREPARATION AND ASYMMETRIC HYDROBORATION OF REPRESENTATIVE CIS-DISUBSTITUTED ALKENES [J].

BROWN, HC ;

DESAI, MC ;

JADHAV, PK .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (26) :5065-5069

[6]

BRUNNER H, 1988, TOP STEREOCHEM, V18, P129

[7] ENANTIOSELECTIVE HYDROBORATIONS CATALYZED BY RHODIUM(+1) COMPLEXES [J].

BURGESS, K ;

VANDERDONK, WA ;

OHLMEYER, MJ .

TETRAHEDRON-ASYMMETRY, 1991, 2 (07) :613-621

[8] ENANTIOSELECTIVE HYDROBORATION MEDIATED BY HOMOCHIRAL RHODIUM CATALYSTS [J].

BURGESS, K ;

OHLMEYER, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :5178-5179

[9] 1ST APPLICATION OF ATTRACTIVE INTRAMOLECULAR INTERACTIONS TO THE DESIGN OF CHIRAL CATALYSTS FOR HIGHLY ENANTIOSELECTIVE DIELS-ALDER REACTIONS [J].

COREY, EJ ;

LOH, TP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8966-8967

[10]

DRIAN CL, 1982, J AM CHEM SOC, V104, P5473

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