Design of Bicyclic and Cage Boron Compounds Based on Allylboration of Acetylenes with Allyldichloroboranes

被引：12

作者：

Erdyakov, Sergey Yu. ^{[1
]}

Ignatenko, Anatolli V. ^{[1
]}

Potapova, Tamara V. ^{[1
]}

Lyssenko, Konstantin A. ^{[2
]}

Gurskii, Mikhail E. ^{[1
]}

Bubnov, Yuri N. ^{[1
,2
]}

机构：

[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia

[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 13期

基金：

俄罗斯基础研究基金会;

关键词：

TRYPROSTATIN B; DERIVATIVES; ALKENES;

D O I：

10.1021/ol900793r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allylboration of acetylenes with allyldichloroboranes has been proposed as a first step of allyl boron-acetylene condensation and a way to design condensation products from stage to stage. The chemistry has been applied to the synthesis of isomeric 3-borabicyclo[3.3.1]non-6-enes transformed into 3-methyl-1-boraadamantane and [5-D]-3-methyl-1-boraadamantane derivatives.

引用

页码：2872 / 2875

页数：4

共 12 条

[1] A convenient method for the generation of allylic dihaloboranes and diallyl(chloro)borane and their application in the allylboration of alkenes and acetylenes [J].

Bubnov, YN ;

Kuznetsov, NY ;

Pastukhov, FV ;

Kublitsky, VV .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (21) :4633-4639

[2]

BUBNOV YN, 2004, ALLYLBORANES SCI SYN, V6, P945

[3] Total synthesis of tryprostatin B: Generation of a nucleophilic prenylating species from a prenylstannane [J].

Depew, KM ;

Danishefsky, SJ ;

Rosen, N ;

SeppLorenzino, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (49) :12463-12464

[4] Regioselectivity of 1,1-dimethylallene allylboration: synthesis of isomeric 6-and 7-methylene-3-borabicyclo[3.3.1]nonanes [J].

Erdyakov, SY ;

Gurskii, ME ;

Ignatenko, AV ;

Bubnov, YN .

MENDELEEV COMMUNICATIONS, 2004, 14 (06) :242-244

[5] Carbometalations of simple alkenes with allyldibromoborane [J].

Frantz, DE ;

Singleton, DA .

ORGANIC LETTERS, 1999, 1 (03) :485-486

[6] Synthesis of 1,2-bis(1-boraadamant-2-yl)ethane derivatives. Crystal structure of the racemic form [J].

Gurskii, ME ;

Pershin, DG ;

Potapova, TV ;

Ponomarev, VA ;

Antipin, MY ;

Starikova, ZA ;

Bubnov, YN .

RUSSIAN CHEMICAL BULLETIN, 2000, 49 (03) :503-507

[7] 2,2′-Ethylenedi-1-boraadamantane -: a new derivative of 1-boraadamantane [J].

Gursky, ME ;

Potapova, TV ;

Bubnov, YN .

RUSSIAN CHEMICAL BULLETIN, 1998, 47 (04) :728-729

[8] HYDRIDE TRANSFER-REACTIONS IN THE SERIES OF 1-BORAADAMANTANE ATE-COMPLEXES [J].

MIKHAILOV, BM ;

GURSKY, ME ;

POTAPOVA, TV ;

SHASHKOV, AS .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 201 (01) :81-88

[9] Total synthesis of gypsetin, deoxybrevianamide E, brevianamide E, and tryprostatin B: Novel constructions of 2,3-disubstituted indoles [J].

Schkeryantz, JM ;

Woo, JCG ;

Siliphaivanh, P ;

Depew, KM ;

Danishefsky, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (51) :11964-11975

[10] Allylboration of alkenes with allyldihaloboranes [J].

Singleton, DA ;

Waller, SC ;

Zhang, ZR ;

Frantz, DE ;

Leung, SW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (41) :9986-9987

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