70278-64-7Relevant articles and documents
Design, synthesis and structure of new chiral squaric acid monoaminoalcohols and diaminoalcohols and their use as catalysts in asymmetric reduction of ketones and diketones
Zhou, Hai-Bing,Zhang, Ji,Lü, Shou-Mao,Xie, Ru-Gang,Zhou, Zhong-Yuan,Choi, Michael C.K,Chan, Albert S.C,Yang, Teng-Kuei
, p. 9325 - 9333 (2007/10/03)
Many chiral squaric acid aminoalcohols and C2-symmetric diaminoalcohols have been synthesized and their in situ formed chiral boron heterocycles have been used as catalysts for the enantioselective reduction of prochiral ketones and diketones by borane to give alcohols with up to 99% enantiomeric excess and 99% yield. The effects of solvent, catalyst-substrate ratio and temperature were also investigated.
ELECTRO-ORGANIC REACTION: PART 28. PREPARATIVE APPLICATIONS OF THE OXALATE CATHODIC CLEAVAGE REACTION INCLUDING ONE-POT CONVERSIONS OF ALDEHYDES AND KETONES
Nazar-ul-Islam,Sopher, David W.,Utley, James H. P.
, p. 2741 - 2748 (2007/10/02)
Alcohols and vicinal diols, when co-electrolysed with oxalate esters, undergo transesterification catalysed by cathodically generated base.Under mild conditions at modest cathodic potentials the esters formed in situ give good yields of the corresponding alkanes and alkenes.Furthermore, because diols (pinacols) and alcohols may be efficiently prepared electrochemically from aldehydes and ketones, a one-pot conversion of the carbonyl compounds into alkanes and alkenes has been devised.The method involves prior electrolysis to alcohol or pinacol, addition of an oxalate ester, and further electrolysis for reductive de-oxygenation.Good results are obtained for aromatic ketones and aldehydes.Several oxalate esters have been used in such reactions; diethyloxalate is the most convenient.Esters of squaric acid and of oxamic acid undergo cathodic de-oxygenation but are not convenient in preparative use.