4061-29-4Relevant articles and documents
Flexible stereoselective functionalizations of ketones through umpolung with hypervalent iodine reagents
Mizar, Pushpak,Wirth, Thomas
supporting information, p. 5993 - 5997 (2014/06/10)
The functionalization of carbonyl compounds in the α-position has gathered much attention as a synthetic route because of the wide biological importance of such products. Through polarity reversal, or "umpolung", we show here that typical nucleophiles, such as oxygen, nitrogen, and even carbon nucleophiles, can be used for addition reactions after tethering them to enol ethers. Our findings allow novel retrosynthetic planning and rapid assembly of structures previously accessible only by multistep sequences. A Nu approach: An efficient α-functionalization of ketones with a range of simple and useful nucleophiles is possible by using hypervalent iodine reagents (see scheme; Nu′ can be the Nu itself or a protected form of this nucleophile group).
Asymmetric synthesis of β-dialkylamino alcohols by transfer hydrogenation of α-dialkylamino ketones
Kosmalski, Tomasz,Wojtczak, Andrzej,Zaidlewicz, Marek
experimental part, p. 1138 - 1143 (2009/09/27)
Transfer hydrogenation of representative aryl and heteroaryl dialkylaminomethyl ketones with formic acid-triethylamine, catalyzed by RuCl[(R,R)-TsDPEN](η-p-cymene), produces the corresponding β-dialkylamino alcohols, 97-99% ee, in 50-73% yields. Asymmetric synthesis of (R)-macromerine, 98% ee, the cactus Coryphantha macromeris alkaloid, is also described.
Boranes in Synthesis. 2. Asymmetric Synthesis of β-Amino Alcohols. A Facile Conversion of 2-Amino Acetophenones to the Corresponding β-Amino Alcohols in High Enantiomeric Purity
Beardsley, David A.,Fisher, Gary B.,Goralski, Christian T.,Nicholson, Lawrence W.,Singaram, Bakthan
, p. 1511 - 1514 (2007/10/02)
The asymmetric reduction of 2-amino acetophenones with Ipc2BH or Ipc2BCl at -78 deg C, yields the corresponding β-amino alcohols in good to excellent yields.Although only modest (12-45percent ee) enantiomeric excesses were obtained with Ipc2BH, 75-99perce