Diastereoselective synthesis of 1,2,3-substituted potassium cyclopropyl trifluoroborates via an unusual zinc-boron exchange

被引：29

作者：

Charette, AB ^{[1
]}

Mathieu, S ^{[1
]}

Fournier, JF ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Stn Downtown, Montreal, PQ H3C 3J7, Canada

来源：

SYNLETT | 2005年 / 11期

关键词：

carbenoids; zinc; cycloaddition; cross-coupling; diastereoselectivity;

D O I：

10.1055/s-2005-871557

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoselective cyclopropanation of an allylic alcohol with a gem-dizinc carbenoid followed by an unusual zinc-boron exchange and further treatment with excess KHF2 afforded 1,2,3-syn-cis-substituted cyclopropyl trifluoroborates in 58-63% overall yields. The potassium cyclopropyl trifluoroborates underwent Suzuki-Miyaura cross-coupling reactions to give 1,2,3-functionalized cyclopropanes in good yields. Finally, an oxidation-epimerization sequence gave access to 1,2,3-trans-substituted cyclopropyl trifluoroborate.

引用

页码：1779 / 1782

页数：4

共 46 条

[31] Development of the Suzuki-Miyaura cross-coupling reaction: Use of air-stable potassium alkynyltrifluoroborates in aryl alkynylations [J].

Molander, GA ;

Katona, BW ;

Machrouhi, F .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (24) :8416-8423

[32] Efficient ligandless palladium-catalyzed Suzuki reactions of potassium aryltrifluoroborates [J].

Molander, GA ;

Biolatto, B .

ORGANIC LETTERS, 2002, 4 (11) :1867-1870

[33] Cross-coupling reactions of potassium alkyltrifluoroborates with aryl and 1-alkenyl trifluoromethanesulfonates [J].

Molander, GA ;

Ito, T .

ORGANIC LETTERS, 2001, 3 (03) :393-396

[34] Suzuki cross-coupling reactions of potassium alkenyltrifluoroborates [J].

Molander, GA ;

Rivero, MR .

ORGANIC LETTERS, 2002, 4 (01) :107-109

[35] Synthesis and pharmacological characterization of all sixteen stereoisomers of 2-(2'-carboxy-3'-phenylcyclopropyl)glycine. Focus on (2S,1'S,2'S,3'R)-2-(2'-carboxy-3'-phenylcyclopropyl)glycine, a novel and selective group II metabotropic glutamate receptors antagonist [J].

Pellicciari, R ;

Marinozzi, M ;

Natalini, B ;

Costantino, G ;

Luneia, R ;

Giorgi, G ;

Moroni, F ;

Thomsen, C .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (11) :2259-2269

[36] Enantiomerically pure cyclopropylboronic esters:: auxiliary- versus substrate-control [J].

Pietruszka, J ;

Witt, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (24) :4293-4300

[37]

Pietruszka J, 1997, SYNLETT, P977

[38] Catalytic enantioselective hydroboration of cyclopropenes [J].

Rubina, M ;

Rubin, M ;

Gevorgyan, V .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (24) :7198-7199

[39] Asymmetric memory at labile, stereogenic boron: Enolate alkylation of oxazaborolidinones [J].

Vedejs, E ;

Fields, SC ;

Hayashi, R ;

Hitchcock, SR ;

Powell, DR ;

Schrimpf, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (11) :2460-2470

[40] CONVERSION OF ARYLBORONIC ACIDS INTO POTASSIUM ARYLTRIFLUOROBORATES - CONVENIENT PRECURSORS OF ARYLBORON DIFLUORIDE LEWIS-ACIDS [J].

VEDEJS, E ;

CHAPMAN, RW ;

FIELDS, SC ;

LIN, S ;

SCHRIMPF, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3020-3027

← 1 2 3 4 5 →