Enantioselective Preparation of γ ‐Amino Acids and γ ‐Lactams from Nitro Olefins and Carboxylic Acids, with the Valine‐Derived 4‐Isopropyl‐5,5‐diphenyl‐1,3‐oxazolidin‐2‐one as an Auxiliary

Effect of the Substituent and Amino Group Position on the Lipase‐Catalyzed Resolution of γ‐Amino Esters: A Molecular Docking Study Shedding Light on Candida antarctica lipase B Enantioselectivity

“…13 C NMR (50 MHz, CD 3 OD) δ=17.5, 28.8, 34.8, 38.1, 39.4, 79.9, 158.5, 180.1. Spectral data 1 H and 13 C NMR are consistent with the literature [28] . LC‐HRMS (ESI‐QTOF) calculated for [C 10 H 19 NO 4 ] + requires 217.1314, found 217.1323.…”

“…Following chromatographic separation of the crude mixture, the enantiomeric excesses ( ee ) for the unreacted amino esters 5 a – c were measured by chiral gas phase chromatography, while the ee for the hydrolyzed products 6 a – c were determined by chiral gas phase chromatographic analysis of their ester derivatives 7 a – c . The absolute configurations were assigned by comparison of optical rotation with reported values for the products 6 a , [8b] 8 a , [27] 6 b , and 6 c [28] (Scheme 2).…”

“…Colorless resin. [α] D 20 =−7.6 ( c 1, CHCl 3 ); 35.6 % ee {lit [28] . ( R )‐[α] D 20 =−15.5 (c 1.04, CHCl 3 )}, 1 H NMR (200 MHz, CD 3 OD) δ=1.16 (d, J =7 Hz, 3H, C H 3 CH); 1.43 (s, 9H, [(C H 3 ) 3 C]); 1.41–1.62 (m, 1H, CHC H 2A ); 1.74–1.92 (m, 1H, CHC H 2B ); 2.36–2.53 (m, 1H, C H ); 3.08 (t , J =7.2 Hz, 2H, C H 2 NH).…”

"Syn-effect” in asymmetric vinylogous alkylation of 3-[4-(N-phthalimide)-but-2-enoyl]oxazolidinone

“…Removal of chiral oxazolidinone and N-deprotection of amino group gave the -substituted -amino acid. [15][16][17][18][19][20][21][22] Figure 1. Syn-effect promotor of unfavored Z-alkenes.…”

Seven-Step Total Synthesis of Sporothriolide

“…The synthesis of 1 commenced with the preparation of N -acyl oxazolidinone 14 from the commercially available carboxylic acid 15 and the oxazolidinone lithium salt 16 by the mixed anhydride method using pivaloyl chloride (Scheme ). , To achieve the total synthesis with as few steps as possible, we first examined the Seebach asymmetric Michael addition of 14 to methyl ( E )-3-nitroacrylate 17 , , since the resulting product 18 had the possibility to be directly converted into 10 (X = NO 2 , see Scheme ) by asymmetric dihydroxylation followed by in situ bis-lactonization. The Michael addition of 14 to 17 , however, gave a complex mixture from which the desired adduct 18 was isolated in a modest yield of 29%; both 14 and 17 were consumed completely in this reaction.…”