ChemInform Abstract: Selective Reduction of Carbonyl Compounds with Al‐Alkoxydiisobutylalanes.

Abstract

SelectiveReduction of Carbonyl Compounds with Al-Alkoxydiisobutylalanes.-The title alanes, e.g. iBu 2 Al-O-Et, only reduce aldehydes and ketones such as (I), (III), (V), and (VII), whereas esters, nitriles and acid chlorides are not attacked. Highly chemoselective discrimination between structurally different ketones, c.f. (IX)/(X), between aldehydes and ketones, c.f. (Ia)/(Id), and between aldehydes, c.f. (Ib)/(XIII), is possible. Stereoselective reductions are achieved using iBu 2 Al-O-iPr. -(CHA, J. S.; KWON, O. O.; KIM, J. M.; CHUN, J. H.; LEE, Y. S.; LEE, H. S.; CHO, S. D.; Bull.

Regiospecific Ring-Opening of Unsymmetrical Epoxides to the Corresponding Less Substituted Alcohols by Newly-Devised Meerwein-Ponndorf-Verley Type Reagents

“…Recently, there have appeared a series of diisobutylaluminum derivatives, such as diisobutylhaloalanes (1), [7][8][9][10][11] diisobutylalkoxyalanes (2), [11][12][13][14] diisobutylaminoalanes (3), [15][16][17] diisobutylacetoxyalanes (4 and 5), [49] and diisobutylmethanesulfonylalanes (6 and 7), [18][19][20][21][22] which were prepared by simple reaction of diisobutylaluminum hydride (DIBAH) with the corresponding hydrogen halides , alcohols, amines, acetic acids, and methanesulfonic acids, respectively (Eq. 1-7).…”

“…24 Professor Brown and his coworkers devised diisopinocampheylchlorob- orane (Ipc 2 BCl) (9), which is the outcome from a strategic modification of the electronic and steric environments of the boron in trialkylboranes can reduce a variety of ketones as well as aldehydes to the corresponding alcohols even at -25 o C. Soon other mono-and diisopinocampheylhaloboranes (10 and 11), were also prepared. [25][26][27][28][29] Furthermore, hydroxy-, alkoxy-, acetoxyand methanesulfonyl-incorporated diisopinocampheylborane derivatives (12)(13)(14)(15)(16)(17) were prepared and their applicability in MPV type reduction was explored. [30][31][32][33][34][35][36]…”