141550-13-2Relevant articles and documents
Direct synthesis of functionalized allylic boronic esters from allylic alcohols and inexpensive reagents and catalysts
Dutheuil, Guillaume,Selander, Nicklas,Szabo, Kalman J.,Aggarwal, Varinder K.
, p. 2293 - 2297 (2008)
A remarkably simple and effective system for the direct conversion of allylic alcohols into high value allylic boronic esters using commercially available reagents and catalysts is described. Georg Thieme Verlag Stuttgart.
Regio- and stereoselective synthesis of allylboranes via platinum(0)- catalyzed borylation of allyl halides with pinacolborane
Murata, Miki,Watanabe, Shinji,Masuda, Yuzuru
, p. 5877 - 5880 (2000)
Various allyl halides were borylated with pinacolboranes in the presence of NEt3 and a catalytic amount of Pt(dba)2 and AsPh3 to afford regio- and stereodefined allylboranes in good yields. (C) 2000 Elsevier Science Ltd.
Stereoselective Dehydroxyboration of Allylic Alcohols to Access (E)-Allylboronates by a Combination of C-OH Cleavage and Boron Transfer under Iron Catalysis
Su, Wei,Wang, Ting-Ting,Tian, Xia,Han, Jian-Rong,Zhen, Xiao-Li,Fan, Shi-Ming,You, Ya-Xin,Zhang, Yu-Kun,Qiao, Rui-Xiao,Cheng, Qiushi,Liu, Shouxin
supporting information, p. 9094 - 9099 (2021/11/30)
Iron-catalyzed direct SN2′ dehydroxyboration of allylic alcohols has been developed to access (E)-stereoselective allylboronates. Allylic alcohols with diverse structures and functional groups, especially derived from natural products, underwent smooth transformation. The six-membered ring transition state formed by allylic alcohols and iron-boron intermediate was indicated to be the key component involved in transfer of the boron group, activation of the C-OH bond, and control of the stereoselectivity.
A Catalytic Dual Isomerization/Allylboration Sequence for the Stereoselective Construction of Congested Secondary Homoallylic Alcohols
Liu, Yangbin,Mazet, Clément
, p. 5638 - 5650 (2020/05/19)
A catalytic sequence for the diastereo- and enantioselective preparation of homoallylic alcohols with an adjacent quaternary (stereo)center is reported. The one-pot process relies on the use of a single (achiral or chiral) iridium complex to catalyze the concomitant isomerization of primary allylic alcohols and homoallylboronates into (chiral) aldehydes and allylboronates, respectively. In the same flask, a chiral Br?nsted acid is added next to engage the isomerization products into a stereocontrolled allylboration reaction. Structural variations have been performed on both the allylic alcohols and the homoallylboronates. This mild process affords an array of stereochemically congested and complex chiral secondary homoallylic alcohols in high yield, excellent diastereoselectivity, and usually high enantioselectivity.