HETEROGENEOUS CATALYTIC ASYMMETRIC DIHYDROXYLATION OF OLEFINS - A NEW POLYMERIC SUPPORT AND A PROCESS IMPROVEMENT

被引：41

作者：

PINI, D ^{[1
]}

PETRI, A ^{[1
]}

SALVADORI, P ^{[1
]}

机构：

[1] UNIV PISA,CNR,CTR STUDIO MACROMOLEC STEREORDINATE & OTTICAMENTE,DIPARTIMENTO CHIM & CHIM IND,I-56126 PISA,ITALY

来源：

TETRAHEDRON | 1994年 / 50卷 / 38期

关键词：

D O I：

10.1016/S0040-4020(01)89433-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new polymeric support containing a derivative of quinine 4-chlorobenzoate and alcoholic pendent groups was found to give good enantioselectivity in many cases comparable to those obtained with the free alkaloid in homogeneous reaction conditions, providing also the known advantages of the heterogeneous process. Both aromatic and aliphatic olefins were screened, using either N-methylmorpholine-N-oxide (NMO) or potassium ferricyanide (K3Fe(CN)(6)) as secondary oxidants.

引用

页码：11321 / 11328

页数：8

共 19 条

[1] RECENT DEVELOPMENTS IN THE APPLICATION OF FUNCTIONALIZED POLYMERS IN ORGANIC-SYNTHESIS [J].

AKELAH, A ;

SHERRINGTON, DC .

POLYMER, 1983, 24 (11) :1369-1386

[2]

AKELAH A, 1981, SYNTHESIS-STUTTGART, P413

[3] IMPROVED ENANTIOSELECTIVITY IN ASYMMETRIC DIHYDROXYLATIONS OF TERMINAL OLEFINS USING PYRIMIDINE LIGANDS [J].

CRISPINO, GA ;

JEONG, KS ;

KOLB, HC ;

WANG, ZM ;

XU, DQ ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3785-3786

[4] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[5] ASYMMETRIC INDUCTION IN THE BASE-CATALYZED REACTIONS USING POLYMER-SUPPORTED QUININES WITH SPACER GROUPS [J].

INAGAKI, M ;

HIRATAKE, J ;

YAMAMOTO, Y ;

ODA, J .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (11) :4121-4126

[6] PROTECTION AND POLYMERIZATION OF FUNCTIONAL MONOMERS .13. ANIONIC LIVING POLYMERIZATION OF TERT-BUTYL 4-VINYLBENZOATE [J].

ISHIZONE, T ;

HIRAO, A ;

NAKAHAMA, S .

MACROMOLECULES, 1989, 22 (07) :2895-2901

[7] ASYMMETRIC DIHYDROXYLATION VIA LIGAND-ACCELERATED CATALYSIS [J].

JACOBSEN, EN ;

MARKO, I ;

MUNGALL, WS ;

SCHRODER, G ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) :1968-1970

[8]

KIM BM, 1990, TETRAHEDRON LETT, V31, P3003

[9]

KWONG HL, 1990, TETRAHEDRON LETT, V31, P2999

[10] USE OF INSOLUBLE POLYMER SUPPORTS IN ORGANIC CHEMICAL SYNTHESIS [J].

LEZNOFF, CC .

CHEMICAL SOCIETY REVIEWS, 1974, 3 (01) :65-85

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