18069-22-2Relevant articles and documents
Enantioselective Acyloin Rearrangement of Acyclic Aldehydes Catalyzed by Chiral Oxazaborolidinium Ion
Cho, Soo Min,Lee, Si Yeon,Ryu, Do Hyun
, p. 1516 - 1520 (2021/03/03)
A catalytic enantioselective acyloin rearrangement of acyclic aldehydes to synthesize highly optically active acyloin derivatives is described. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction provided chiral α-hydroxy aryl ketones in high yield (up to 95%) and enantioselectivity (up to 98% ee). In addition, the enantioselective acyloin rearrangement of α,α-dialkyl-α-siloxy aldehydes produced chiral α-siloxy alkyl ketones in high yield (up to 92%) with good enantioselectivity (up to 89% ee).
Synthesis and reactivity of enantiomerically enriched thiiranium ions
Denmark, Scott E.,Vogler, Thomas
supporting information; experimental part, p. 11737 - 11745 (2010/06/12)
Enantiomerically enriched thiiranium ion 5 has been prepared by silverassisted ionization of chloro sulfide 4 at -20°C. This thiiranium ion is configurationally stable in solution up to room temperature as demonstrated by the stereospecific capture of the ion by various oxygen- and nitrogen-based nucleophiles. Both isolated olefins and weak Lewis bases can promote the racemization of 5 but these processes can also be suppressed at low temperature. Capture of 5 by methanol is faster than the racemization processes.
Modular asymmetric synthesis of 1,2-diols by single-pot allene diboration/hydroboration/cross-coupling
Pelz, Nicholas F.,Morken, James P.
, p. 4557 - 4559 (2007/10/03)
Chiral allyl vinyl boronates are generated by catalytic enantioselective diboration of prochiral allenes. They may then be reacted, in situ, with a hydroborating reagent to form a novel triboron intermediate. The least hindered and most reactive C-B bond
