17180-62-0Relevant articles and documents
Benchtop-Stabssle Hypervalent Bromine(III) Compounds: Versatile Strategy and Platform for Air- And Moisture-Stable λ3-Bromanes
Miyamoto, Kazunori,Saito, Motomichi,Tsuji, Shunsuke,Takagi, Taisei,Shiro, Motoo,Uchiyama, Masanobu,Ochiai, Masahito
supporting information, p. 9327 - 9331 (2021/07/01)
We present the first synthesis of air/moisture-stable λ3-bromanes (9and10) by using a cyclic 1,2-benzbromoxol-3-one (BBX) strategy. X-ray crystallography and NMR and IR spectroscopy ofN-triflylimino-λ3-bromane (12) revealed that the bromine(III) center is effectively stabilized by intramolecular R-Br-O hypervalent bonding. This strategy enables the synthesis of a variety of air-, moisture-, and benchtop-stable Br-hydroxy, -acetoxy, -alkynyl, -aryl, and bis[(trifluoromethyl)sulfonyl]methylide λ3-bromane derivatives.
Convenient methods for the preparation of unsymmetrical double aldols
Mukaiyama, Teruaki,Pudhom, Khanitha,Yamane, Keiko,Arai, Hidehiro
, p. 413 - 425 (2007/10/03)
Double aldol reaction proceeded stereoselectively at one α-carbon of ketones to give α-(1-hydroxyalkyl)-β-hydroxyalkyl ketones (double aldols) in good to high yields by the following three methods: i) tin(II) trifluoromethanesulfonate-mediated aldol reaction of aldehydes with β-hydroxy ketones (mono-aldols) in the presence of tertiary amines, ii) samarium(II) iodide-mediated aldol reaction of aldehydes with alkyl or aryl oxiranyl ketones, iii) Sn(OTf)2- promoted aldol reaction of α-bromo ketones with aldehydes giving α-bromo-β-stannyloxy ketones which were then converted to titanium enolates on treatment with low-valent titanium. Double aldols were formed by subsequent reaction of the above titanium enolates with aldehydes in one-pot procedure. Further, small and medium-sized carbocyclic compounds whose ring skeletons were composed of double aldol structure were synthesized by SmI2-mediated intramolecular cyclization between oxiranyl ketone and aldehyde functions.
The first catalytic enantioselective synthesis of cis-epoxyketones from cis-enones
Watanabe,Arai,Sasai,Bougauchi,Shibasaki
, p. 8090 - 8091 (2007/10/03)
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