Regiochemistry of Wacker-type oxidation of vinyl group in the presence of neighboring oxygen functions .2.

被引：29

作者：

Pellissier, H

Michellys, PY

Santelli, M

机构：

[1] Lab. de Synthèse Organique, ESA no 6009, Centre de St.-Jérôme, 13397 Marseille Cedex 20, Av. Esc. Normandie-Niemen

来源：

TETRAHEDRON | 1997年 / 53卷 / 31期

关键词：

D O I：

10.1016/S0040-4020(97)00777-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regioselectivity of the palladium(II) oxidation of (+/-)-17 alpha-vinyl-1,3,5(10)-gonatriene derivatives bearing a lactonic bridge on the alpha or beta-face (beta-face: obtention of the expected acetyl derivatives; alpha-face: presence of aldehydes, anti-Markovnikov addition) may be rationalized by an intramolecular coordination of the metal with the two lactonic oxygen atoms. Calculations carried out using ZINDO I method confirm the existence of such a chelation and the possibility of a cis-hydroxy or a cis-acetoxypalladation in the course of the Wacker process. An experimental confirmation was given by the regioselective mono-oxidation of the vinyl group syn to the methoxycarbonyl group of (3R*,6S*,9S*)-3-methoxycarbonyl-3-(2-propyl)-6,9-divinyl-1-oxaspiro[4.4]nonan-2-one. (C) 1997 Published by Elsevier Science Ltd.

引用

页码：10733 / 10742

页数：10

共 53 条

[21] PALLADIUM(II)-CATALYZED ALKOXYLATION AND ACETOXYLATION OF ALKENES [J].

HOSOKAWA, T ;

SHINOHARA, T ;

OOKA, Y ;

MURAHASHI, SI .

CHEMISTRY LETTERS, 1989, (11) :2001-2004

[22] ELECTROCHEMICAL WACKER TYPE REACTION WITH A DOUBLE MEDIATORY SYSTEM CONSISTING OF PALLADIUM COMPLEX AND TRI(4-BROMOPHENYL)AMINE [J].

INOKUCHI, T ;

PING, L ;

HAMAUE, F ;

IZAWA, M ;

TORII, S .

CHEMISTRY LETTERS, 1994, (01) :121-124

[23]

JIRA R, 1996, APPL HOMOGENEOUS CAT, V1, P374

[24] COMPLETE REVERSE REGIOSELECTION IN WACKER OXIDATION OF ACETONIDES AND CYCLIC CARBONATES OF ALLYLIC DIOLS [J].

KANG, SK ;

JUNG, KY ;

CHUNG, JU ;

NAMKOONG, EY ;

KIM, TH .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4678-4679

[25] ORGANIC-SYNTHESIS WITH ENZYMES .3. TBADH-CATALYZED REDUCTION OF CHLORO KETONES - TOTAL SYNTHESIS OF (+)-(S,S)-(CIS-6-METHYLTETRAHYDROPYRAN-2-YL)ACETIC ACID - A CIVET CONSTITUENT [J].

KEINAN, E ;

SETH, KK ;

LAMED, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (12) :3474-3480

[26] COMPARATIVE-STUDY ON CATALYTIC-OXIDATION OF ETHYLENE BY PALLADIUM(II) IN AQUEOUS AND ACETIC-ACID SOLUTIONS [J].

KOSAKI, M ;

ISEMURA, M ;

KITAURA, Y ;

SHINODA, S ;

SAITO, Y .

JOURNAL OF MOLECULAR CATALYSIS, 1977, 2 (05) :351-359

[27] AN EFFICIENT SYNTHESIS OF GAMMA/DELTA KETO ESTERS [J].

KULKARNI, MG ;

SEBASTIAN, MT .

SYNTHETIC COMMUNICATIONS, 1991, 21 (04) :581-586

[28] REVERSAL OF REGIOCHEMISTRY OF WACKER-TYPE REACTIONS ORIENTED BY HETEROATOMS [J].

LAI, JY ;

SHI, XX ;

DAI, LX .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3485-3487

[29] PALLADIUM(II)-CATALYZED SYNTHESIS OF OPTICALLY-ACTIVE TETRAHYDRO-1,4-OXAZINE DERIVATIVES [J].

LAI, JY ;

SHI, XX ;

GONG, YS ;

DAI, LX .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) :4775-4777

[30] CHEMOENZYMATIC SYNTHESIS OF NATURAL-PRODUCTS - SYNTHESIS OF SPHYDROFURAN [J].

MALIAKEL, BP ;

SCHMID, W .

TETRAHEDRON LETTERS, 1992, 33 (23) :3297-3300

← 1 2 3 4 5 6 →