30169-75-6Relevant academic research and scientific papers
How Big is the Pinacol Boronic Ester as a Substituent?
Fasano, Valerio,McFord, Aidan W.,Butts, Craig P.,Collins, Beatrice S. L.,Fey, Natalie,Alder, Roger W.,Aggarwal, Varinder K.
supporting information, p. 22403 - 22407 (2020/10/12)
The synthetically versatile pinacol boronic ester group (Bpin) is generally thought of as a bulky moiety because of the two adjacent quaternary sp3-hydribized carbon atoms in its diol backbone. However, recent diastereoselective reactions repor
ORGANOBORANES. 32. HOMOLOGATION OF ALKYLOBORONIC ESTERS WITH METHOXY(PHENYLTHIO)METHYLLITHIUM: REGIO- AND STEREOCONTROLLED ALDEHYDE SYNTHESIS FROM OLEFINS VIA HYDROBORATION.
Brown,Imai
, p. 6285 - 6289 (2007/10/02)
Homologation of 2-alkyl-1,3,2-dioxaborinanes, RBO//2C//3H//6 (1), to alpha -methoxyalkyl derivatives, RCH(OMe) BO//2C//3H//6 (2), was achieved by reaction with LiCH(OMe) SPh, followed by treatment with HgCl//2. The intermediates 2 were smoothly oxidized with hydrogen peroxide in a pH 8 phosphate buffer to give the corresponding aldehydes, RCHO (3). The alkyl groups of 1 were introduced by the hydroboration method. Thus, heptanal, 3-phenylbutanal, 2-ethylpentanal, cyclohexanecarbaldehyde, trans-2-methylcyclopentanecarbaldehyde, and exo-norbornanecarbaldehyde were prepared in fair to good yields from 1-hexene, 2-phenylpropene, 3-hexene, cyclohexene, 1-methylcyclopentene, and norbornene, respectively. Furthermore, both threo- and erythro-2,-dimethylpentanal were obtained in 96% diastereomeric purity from (E)- and (Z)-3-methyl-2-pentene, respectively. The migration of the alkyl group from boron to carbon proceeds with retention of configuration.
