133271-12-2Relevant academic research and scientific papers
Catalytic Asymmetric Iterative/Domino Aldehyde Cross-Aldol Reactions for the Rapid and Flexible Synthesis of 1,3-Polyols
Lin, Luqing,Yamamoto, Kumiko,Mitsunuma, Harunobu,Kanzaki, Yamato,Matsunaga, Shigeki,Kanai, Motomu
supporting information, p. 15418 - 15421 (2015/12/26)
We report here catalytic asymmetric iterative and domino cross-aldol reactions between aldehydes, endowed with a high level of robustness, flexibility, and generality. A Cu(I)-DTBM-SEGPHOS complex catalyzes an asymmetric cross-aldol reaction between acceptor aldehydes and boron enolates derived from donor aldehydes, which are generated through Ir-catalyzed isomerization of allyloxyboronates. The unit process can be repeated using the aldol products in turn as acceptor substrates for the subsequent asymmetric aldol reaction. The donor aldehydes and stereoselectivity can be flexibly switched in a stepwise manner for the double-aldol reaction. Furthermore, asymmetric triple- and quadruple-aldol reactions are possible in one-pot using the appropriate amounts of donors and amine additives, rapidly elongating the carbon skeleton with controlling up to eight stereocenters. The method should be useful for straightforward synthesis of enantiomerically and diastereomerically enriched 1,3-polyols.
Novel enantioselective direct aldol-type reaction promoted by a chiral phosphine oxide as an organocatalyst
Kotani, Shunsuke,Shimoda, Yasushi,Sugiura, Masaharu,Nakajima, Makoto
supporting information; experimental part, p. 4602 - 4605 (2009/10/26)
Chiral phosphine oxide successfully catalyzed the direct aldol-type reactions of cyclohexanone derivatives and benzaldehyde derivatives in high stereoselectivities. The reaction mechanism involves the in situ formation of trichlorosilyl enol ethers. The present reaction could be extended to the cross-aldol reactions between two aldehydes.
