92945-17-0Relevant 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.
Regioselective Alkyl and Alkynyl Substitution Reactions of Epoxy Alcohols by the Use of Organoaluminum Ate Complexes: Regiochemical Reversal of Nucleophilic Substitution Reactions
Sasaki, Minoru,Tanino, Keiji,Miyashita, Masaaki
, p. 1765 - 1767 (2007/10/03)
(matrix presented) Unprecedented nucleophilic substitution reactions of 2,3-epoxy-1-alkanols with alkyl- and alkynylaluminum ate complexes have been studied and demonstrated to occur at the C2 position with extremely high stereoselectivity, i.e., with exa
Scope and Stereochemical Course of the Addition of (Trimethylsilyl)allenes to Ketones and Aldehydes. A Regiocontrolled Synthesis of Homopropargylic Alcohols
Danheiser, Rick L.,Carini, David J.,Kwasigroch, Carrie A.
, p. 3870 - 3878 (2007/10/02)
The reaction of (trimethylsilyl)allenes with aldehydes and ketones in the presence of titanium tetrachloride provides a regiocontrolled route to homopropargylic alcohols of a variety of substitution types.The addition of 1-alkyl-substituted (trimethylsilyl)allenes to carbonyl compounds furnishes the desired acetylenes directly, while reactions involving allenylsilanes 6,7, and 9 initially produce mixtures of acetylenes and (trimethylsilyl)vinyl chloride derivatives.Exposure of these mixtures to the action of potassium fluoride in dimethyl sulfoxide then generates the desired homopropargylic alcohols.The addition of the chiral allenylsilane 9 to achiral aldehydes has been found to proceed with modest (3-4:1) diastereoselectivity to produce mainly syn (erythro) homopropargylic alcohols.
Stereoselective Reduction of α-Methyl-β-hydroxy Ketones with Zinc Borohydride
Nakata, Tadashi,Tani, Yoichiro,Hatozaki, Masayoshi,Oishi, Takeshi
, p. 1411 - 1415 (2007/10/02)
Zinc borohydride reduction of α-methyl-β-hydroxy ketones 3 produced the erythro-2-methyl-1,3-glycol derivatives 4 with high stereoselectivity.The selectivity was particularly high when an olefinic group was conjugated to the carbonyl group.Reduction of th
