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

[1]

Boudier A, 2000, CHEM-EUR J, V6, P2748, DOI 10.1002/1521-3765(20000804)6:15<2748::AID-CHEM2748>3.0.CO

[2]

2-Q

[3]

Boudier A, 2000, ANGEW CHEM INT EDIT, V39, P4414, DOI 10.1002/1521-3773(20001215)39:24<4414::AID-ANIE4414>3.0.CO

[4]

2-C

[5]

BUBNOV YN, 1971, TETRAHEDRON LETT, P2153

[6] First evidence for the formation of a geminal dizinc carbenoid: A highly stereoselective synthesis of 1,2,3-substituted cyclopropanes [J].

Charette, AB ;

Gagnon, A ;

Fournier, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (03) :386-387

[7] Synthesis of contiguous cyclopropanes by palladium-catalyzed Suzuki-type cross-coupling reactions. [J].

Charette, AB ;

DeFreitasGil, RP .

TETRAHEDRON LETTERS, 1997, 38 (16) :2809-2812

[8] A novel Suzuki-type cross-coupling reaction of cyclopropylboronic esters with benzyl bromides [J].

Chen, H ;

Deng, MZ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (10) :1609-1613

[9] A novel stereocontrolled synthesis of 1,2-trans cyclopropyl ketones via Suzuki-type coupling of acid chlorides with cyclopropylboronic acids [J].

Chen, H ;

Deng, MZ .

ORGANIC LETTERS, 2000, 2 (12) :1649-1651

[10] Sliver oxide mediated palladium-catalyzed cross-coupling reaction of cyclopropylboronie acids with allylic bromides [J].

Chen, H ;

Deng, MZ .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) :4444-4446

← 1 2 3 4 5 →