120850-91-1Relevant articles and documents
-
Buck,Ide
, p. 820 (1932)
-
Efficient syntheses of enantiomerically pure 1,2-dicyclohexenyl- and 1,2-dicyclohexyl-1,2-ethanediol using B-2-cyclohexen-1-yl- diisopinocampheylborane
Chen, Guang-Ming,Ramachandran, P. Veeraraghavan
, p. 3935 - 3938 (1997)
The reaction of (+)-B-2-cyclohexen-1-yldiisopinocampheylborane with glyoxal at -78°C yields 98% stereoisomerically pure (1S,2S,1'R,1''R)-(+)- 1,2-bis(2-cyclohexenyl)-1,2-ethanediol in 81% yield. A simple crystallization of the above diol from hexane follo
Facile pinacol coupling of aliphatic ketones by Brook rearrangement in the presence of samarium species
Wang, Xincan,Xie, Guanqun,Zhao, Yanfei,Zheng, Ke,Fang, Yanxiong,Wang, Xiaoxia
supporting information, (2021/04/27)
Herein we report a practical pinacol coupling reaction, in which ketones (aldehydes) react smoothly with Sm and TMSBr to afford the diol products with Sm(II) or (III) siliyl species generated in situ. This reported method affords poor yields for aromatic ketone substrates and good yields for aliphatic ketones. Therefore, it distinguishes from most reductive coupling approaches that are more effective for aromatic carbonyl compounds and provides a facile and robust approach for the pinacol coupling of aliphatic ketones. Mechanistic studies also indicated the pinacolization probably proceeded via an anionic instead of radical coupling pathway involving the Brook rearrangement in the presence of samarium (II or III) silyl species.
Pinacol couplings of a series of aldehydes and ketones with SmI2/Sm/Me3SiCl in DME
Yoshimura, Aya,Saeki, Tomokazu,Nomoto, Akihiro,Ogawa, Akiya
, p. 5347 - 5355 (2015/07/15)
The pinacol coupling is one of the most significant methods to synthesize vic-diols. The combination of samarium diiodide (SmI2) and samarium metal successfully induces the selective pinacol couplings of not only aromatic aldehydes and ketones but also aliphatic ones in the presence of trimethylchlorosilane (Me3SiCl) in 1,2-dimethoxyethane (DME). DME is the most suitable solvent for the reduction system using SmI2 and Me3SiCl. Me3SiCl, a widely available additive, prevents the decomposition of the formed vic-diols, i.e., meso-isomers, and controls their stereochemistry. In particular, the pinacol couplings of sterically hindered aliphatic aldehydes and ketones proceed with excellent diastereoselectivities to afford dl-isomers in good yields.
A new Yb3+-catalyzed pinacol and imine-coupling reaction
Aspinall, Helen C.,Greeves, Nicholas,Hin, Shane Lo Fan
experimental part, p. 1558 - 1561 (2010/06/13)
Ytterbium triflate, Yb(OTf)3, catalyzes the intermolecular reductive homocouplings of imines, aldehydes, and ketones at loadings of 5 mol % in the presence of Mg and Me3SiCl to give isolated yields of up to 95%. Diastereoselectivity of up to 4/96 (dl/meso) is achieved for aromatic aldehydes, up to 100% dl for aliphatic aldehydes, and 100% dl for an intramolecular imine coupling.