Stereoselectivity control in the Rh(I)-catalyzed conjugate additions of aryl and alkenylboronic acids to unprotected hydroxycyclopentenones

被引：26

作者：

de la Herrán, G ^{[1
]}

Mba, M ^{[1
]}

Murcia, MC ^{[1
]}

Plumet, J ^{[1
]}

Csáky, AG ^{[1
]}

机构：

[1] Univ Complutense, Fac Quim, Dept Quim Organ, E-28040 Madrid, Spain

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 08期

关键词：

D O I：

10.1021/ol050462n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective Rh(I)-catalyzed conjugate addition reaction of aryl and alkenylboronic acids to unprotected 2-phenyl-4-hydroxycyclopentenone is presented. The free OH group on the substrate is responsible for the stereochemistry, which is cis for arylboronic derivatives. In the case of the alkenylboronic compounds, the stereochemistry can be tuned to either a cis (bases as additives) or trans addition (CsF as additive) without the need of protecting groups.

引用

页码：1669 / 1671

页数：3

共 28 条

[1] Chelating bis-carbene rhodium(III) complexes in transfer hydrogenation of ketones and imines [J].

Albrecht, M ;

Crabtree, RH ;

Mata, J ;

Peris, E .

CHEMICAL COMMUNICATIONS, 2002, (01) :32-33

[2] SYNTHESIS AND CHARACTERIZATION OF RH(P(CH3)3)2(CO)CH3 AND RH(P(CH3)3)2(CO)PH [J].

BOYD, SE ;

FIELD, LD ;

HAMBLEY, TW ;

PARTRIDGE, MG .

ORGANOMETALLICS, 1993, 12 (05) :1720-1724

[3]

COLLINS CW, 2003, CHEM REV, V93, P1533

[4] SYNTHESIS AND GASTRIC ANTISECRETORY PROPERTIES OF 15-DEOXY-16-HYDROXYPROSTAGLANDIN E ANALOGS [J].

COLLINS, PW ;

DAJANI, EZ ;

DRISKILL, DR ;

BRUHN, MS ;

JUNG, CJ ;

PAPPO, R .

JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (09) :1152-1159

[5] Catalytic asymmetric hydroboration: Recent advances and applications in carbon-carbon bond-forming reactions [J].

Crudden, CM ;

Edwards, D .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (24) :4695-4712

[6] Enantioselective synthesis of γ,δ-disubstituted β-hydroxy δ-lactones from furans:: Synthesis of (+)-prelactone B and its C-4 epimer [J].

Csáky, AG ;

Mba, M ;

Plumet, J .

SYNLETT, 2003, (13) :2092-2094

[7] Regio- and stereoselective addition of Grignard and organolithium reagents to 4-hydroxy-2-cyclopentenones [J].

Csáky, AG ;

Mba, M ;

Plumet, J .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :9026-9029

[8] ALKYL AND ARYL COMPOUNDS OF IRIDIUM AND RHODIUM .20. PREPARATION AND CHARACTERIZATION OF MESITYLBIS(TRIMETHYLPHOSPHITE)TRIPHENYLPHOSPHINERHODIUM(I) AND MESITYLTRIS(TRIMETHYLPHOSPHITE)RHODIUM(I) [J].

DAHLENBURG, L ;

YARDIMCIOGLU, A ;

HOCK, N .

INORGANICA CHIMICA ACTA-ARTICLES AND LETTERS, 1984, 89 (03) :213-217

[9] Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].

Fagnou, K ;

Lautens, M .

CHEMICAL REVIEWS, 2003, 103 (01) :169-196

[10] CYCLOPENTENONE DERIVATIVES .6. 4-OXO-2-CYCLOPENTENYL ACETATE - A SYNTHETIC INTERMEDIATE [J].

HARRE, M ;

RADDATZ, P ;

WALENTA, R ;

WINTERFELDT, E .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (07) :480-492

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