Palladium-catalyzed reaction of 4-cyclopentene-1,3-diol monoacetate with Grignard reagents producing hitherto unreachable cis-1,2-isomers

被引：12

作者：

Hattori, H

Abbas, AA

Kobayashi, Y

机构：

[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2268501, Japan

[2] Cairo Univ, Fac Sci, Dept Chem, Giza, Egypt

来源：

CHEMICAL COMMUNICATIONS | 2004年 / 07期

关键词：

D O I：

10.1039/b316596e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reaction of 4-cyclopentene-1,3-diol monoacetate with RMgCl (R = alkyl, aryl) in the presence of a palladium catalyst proceeded with retention of configuration to give cis-1,2-regioisomers as the major products.

引用

页码：884 / 885

页数：2

共 31 条

[1]

[Anonymous], J ORG CHEM

[2] STEREOCHEMICAL ASPECTS OF THE NICKEL-CATALYZED ALKYLATION OF ALLYLIC ALCOHOLS [J].

CONSIGLIO, G ;

MORANDINI, F ;

PICCOLO, O .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (07) :1846-1847

[3]

Deardorff D. R., 1993, ORG SYNTH, VVIII, P13

[4] Conversion of allylic alcohols into allylic nitromethyl compounds via a palladium-catalyzed solvolysis: An enantioselective synthesis of an advanced carbocyclic nucleoside precursor [J].

Deardorff, DR ;

Savin, KA ;

Justman, CJ ;

Karanjawala, ZE ;

Sheppeck, JE ;

Hager, DC ;

Aydin, N .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3616-3622

[5] ENANTIOSELECTIVE PREPARATION OF FUNCTIONALIZED CYCLOPENTANOIDS VIA A COMMON CHIRAL (PI-ALLYL)PALLADIUM COMPLEX [J].

DEARDORFF, DR ;

LINDE, RG ;

MARTIN, AM ;

SHULMAN, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) :2759-2762

[6] A PALLADIUM-CATALYZED ROUTE TO MONOPROTECTED AND DIPROTECTED CIS-2-CYCLOPENTENE-1,4-DIOLS [J].

DEARDORFF, DR ;

MYLES, DC ;

MACFERRIN, KD .

TETRAHEDRON LETTERS, 1985, 26 (46) :5615-5618

[7] Hydroxy alkenenitriles: Diastereoselective conjugate addition-alkylations [J].

Fleming, FF ;

Wang, QZ ;

Steward, OW .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4235-4238

[8] γ-hydroxy-α,β-alkenenitriles:: Chelation-controlled conjugate additions [J].

Fleming, FF ;

Wang, QZ ;

Zhang, ZY ;

Steward, OW .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17) :5953-5956

[9] Cyclic alkenenitriles: Synthesis, conjugate addition, and stereoselective annulation [J].

Fleming, FF ;

Zhang, ZY ;

Wang, QZ ;

Steward, OW .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (20) :7646-7650

[10] Unsaturated nitriles: Conjugate additions of carbon nucleophiles to a recalcitrant class of acceptors [J].

Fleming, FF ;

Wang, QZ .

CHEMICAL REVIEWS, 2003, 103 (05) :2035-2077

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