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
收藏
页码：2872 / 2875
页数：4
相关论文
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
    Bubnov, YN
    Kuznetsov, NY
    Pastukhov, FV
    Kublitsky, VV
    [J]. 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
    Depew, KM
    Danishefsky, SJ
    Rosen, N
    SeppLorenzino, L
    [J]. 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
    Erdyakov, SY
    Gurskii, ME
    Ignatenko, AV
    Bubnov, YN
    [J]. MENDELEEV COMMUNICATIONS, 2004, 14 (06) : 242 - 244
  • [5] Carbometalations of simple alkenes with allyldibromoborane
    Frantz, DE
    Singleton, DA
    [J]. 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
    Gurskii, ME
    Pershin, DG
    Potapova, TV
    Ponomarev, VA
    Antipin, MY
    Starikova, ZA
    Bubnov, YN
    [J]. RUSSIAN CHEMICAL BULLETIN, 2000, 49 (03) : 503 - 507
  • [7] 2,2′-Ethylenedi-1-boraadamantane -: a new derivative of 1-boraadamantane
    Gursky, ME
    Potapova, TV
    Bubnov, YN
    [J]. RUSSIAN CHEMICAL BULLETIN, 1998, 47 (04) : 728 - 729
  • [8] HYDRIDE TRANSFER-REACTIONS IN THE SERIES OF 1-BORAADAMANTANE ATE-COMPLEXES
    MIKHAILOV, BM
    GURSKY, ME
    POTAPOVA, TV
    SHASHKOV, AS
    [J]. 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
    Schkeryantz, JM
    Woo, JCG
    Siliphaivanh, P
    Depew, KM
    Danishefsky, SJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (51) : 11964 - 11975
  • [10] Allylboration of alkenes with allyldihaloboranes
    Singleton, DA
    Waller, SC
    Zhang, ZR
    Frantz, DE
    Leung, SW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (41) : 9986 - 9987
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