Wang, Tianli published the artcileRegiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives, Application In Synthesis of 10047-10-6, the main research area is aryl alkyl oxazolone butadienoate chiral phosphine regioselective enantioselective addition; disubstituted oxazolone stereoselective preparation ring opening; amino acid disubstituted stereoselective preparation; alkyl aryl oxazolone butadienoate chiral phosphine regioselective enantioselective addition; oxazolone disubstituted stereoselective preparation reduction; acetal lactol preparation.
Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective γ-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective γ-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronucleophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective γ-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts I (R = Et, Me, n-Pr,i-Pr, n-Bu, etc.; Ar = 4-MeOC6H4, Ph, 4-FC6H4) provided rapid access to optically enriched α,α-disubstituted α-amino acid derivatives, and the C-2-selective products II (R = Et, Me, n-Pr,i-Pr, n-Bu, etc.; Ar = Ph, 2-naphthyl, 1-naphthyl) led to facile synthesis of chiral N,O-acetals and γ-lactols. Theor. studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nucleophilic oxazolide and the electrophilic phosphonium intermediate.
Journal of the American Chemical Society published new progress about Acetals Role: SPN (Synthetic Preparation), PREP (Preparation) (N,O-). 10047-10-6 belongs to class esters-buliding-blocks, name is Methyl 2-aminopentanoate hydrochloride, and the molecular formula is C6H14ClNO2, Application In Synthesis of 10047-10-6.
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