Synthesis of all four homochiral stereoisomers of methyl 3-phenyl-1h-aziridine-2-car☐ylate

Bioresolution Production of (2R,3S)-Ethyl-3-phenylglycidate for Chemoenzymatic Synthesis of the Taxol C-13 Side Chain by Galactomyces geotrichum ZJUTZQ200, a New Epoxide-Hydrolase-Producing Strain

“…Phenylglycidates 2 , 3 , 4 and 5 were synthesized by Darzens reaction [29]. Briefly, methyl chloroacetate (10 mmol) was dissolved in a solution of sodium methoxide (10 mmol) in dry methanol (10 mL) under ice bath cooling and stirred for 5 min, followed by the addition of corresponding aldehyde (5 mmol).…”

3-(3-Cyanophenyl)-N-phenyloxirane-2-carboxamide

“…For the use of epoxide-containing compounds as building blocks in synthesis, see: Meth-Cohn & Chen (1999); Porter & Skidmore (2000); Righi et al (1996); Thijs et al (1990). For related structures, see: Chen & Kang (2009a,b); He (2009); He et al (2009).…”

“…Selective ring opening reactions of oxiranes also provide powerful and efficient routes to a variety of useful compounds including 2,3-epoxyketone (Meth-Cohn et al, 1999), aziridinecarboxylate (Thijs et al, 1990). Various effective systems have been developed over the years for the preparation of chiral epoxides.…”

3-(4-Nitrophenyl)-N-phenyloxirane-2-carboxamide

“…For epoxide-containing compounds used as building blocks in synthesis, see: Righi et al (1996); Bhatia et al (1999); Meth-Cohn et al (1999); Thijs et al (1990).…”

“…Oxiranecarboxamides are the key building blocks in the synthesis of natural products such as the Taxol side chain (Righi et al 1996). Selective ring-opening reactions of oxiranes also provide powerful and efficient routes to a variety of useful compounds including 2,3-epoxyketone (Meth-Cohn et al 1999), aziridinecarboxylate (Thijs et al 1990). isoserine derivatives (Bhatia et al 1999).…”