Enantiomerically pure cyclopropane building blocks: Synthesis and transformations of 2-iodocyclopropylboronic esters

被引：33

作者：

Hohn, E ^{[1
]}

Pietruszka, J ^{[1
]}

机构：

[1] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2004年 / 346卷 / 07期

关键词：

boron; chiral auxiliaries; cross-coupling; cyclopropanes; palladium;

D O I：

10.1002/adsc.200404055

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Enantiomerically pure 2-iodocyclopropyl-boronic esters 6 and 8 have been synthesized from the readily available allylic alcohol 2 via an oxidation-radical decarboxylation sequence. These unique building blocks have been demonstrated to be versatile intermediates for a consecutive Suzuki-coupling with aryl-, heteroaryl-, alkenyl-, and cyclopropylboron derivatives (I example each).

引用

页码：863 / 866

页数：4

共 37 条

[1] THE INVENTION OF NEW RADICAL CHAIN REACTIONS .8. RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS - A NEW METHOD FOR THE GENERATION OF CARBON RADICALS FROM CARBOXYLIC-ACIDS
BARTON, DHR
CRICH, D
MOTHERWELL, WB
[J]. TETRAHEDRON, 1985, 41 (19) : 3901 - 3924
[2] BUBNOV YN, 1971, TETRAHEDRON LETT, P2153
[3] Palladium-catalyzed Suzuki-type cross-couplings of iodocyclopropanes with boronic acids: Synthesis of trans-1,2-dicyclopropyl alkenes
Charette, AB
Giroux, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) : 8718 - 8719
[4] Synthesis of contiguous cyclopropanes by palladium-catalyzed Suzuki-type cross-coupling reactions.
Charette, AB
DeFreitasGil, RP
[J]. TETRAHEDRON LETTERS, 1997, 38 (16) : 2809 - 2812
[5] APPLICATIONS OF CYCLOPROPYLBORANES IN ORGANIC-SYNTHESIS .1. A STEREOCONTROLLED ROUTE TO SUBSTITUTED CYCLOPROPANOL DERIVATIVES
DANHEISER, RL
SAVOCA, AC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) : 2401 - 2403
[6] Introduction: Cyclopropanes and related rings
de Meijere, A
[J]. CHEMICAL REVIEWS, 2003, 103 (04) : 931 - 932
[7] Synthesis of the polycyclopropane antibiotic FR-900848 via the horeau gambit
Falck, JR
Mekonnen, B
Yu, JR
Lai, JY
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (25) : 6096 - 6097
[8] Palladium-catalyzed cross-coupling of stereospecific potassium cyclopropyl trifluoroborates with aryl bromides
Fang, GH
Yan, ZJ
Deng, MZ
[J]. ORGANIC LETTERS, 2004, 6 (03) : 357 - 360
[9] A CONVENIENT HIGHLY STEREOSELECTIVE SYNTHESIS OF CYCLOPROPYLBORONATES
FONTANI, P
CARBONI, B
VAULTIER, M
CARRIE, R
[J]. TETRAHEDRON LETTERS, 1989, 30 (36) : 4815 - 4818
[10] FONTANI P, 1991, SYNTHESIS-STUTTGART, P605

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