592531-07-2Relevant articles and documents
Studies on two different diastereoselective reaction pathways from a serinol derivative to 4-hydroxymethyl-2-oxazolidinones using 2-chloroethyl chloroformate and N,N′-disuccinimidyl carbonate
Sugiyama, Shigeo,Ishii, Keitaro
scheme or table, p. 2904 - 2910 (2011/03/19)
Two reaction pathways and their diastereoselectivity-determining steps of the asymmetric desymmetrization of (R)-2-(α-methylbenzyl)amino-1,3- propanediol 1 with 2-chloroethyl chloroformate (CCF) and with N,N′-disuccinimidyl carbonate giving (4S,αR)-4-hydr
Diastereoselective intramolecular acyl transfer of 5-(α-methylbenzyl)amino-1,3-dioxan-2-one to 4-hydroxymethyl-2-oxazolidinones
Sugiyama, Shigeo,Fukuchi, Haruka,Ishii, Keitaro
, p. 12047 - 12057 (2008/03/13)
Intramolecular acyl transfer of (R)-5-(α-methylbenzyl)amino-1,3-dioxan-2-one (2) by treatment with DBU in CD2Cl2, CDCl3, C6D6, CD3CN, CD3NO2, DMSO-d6, DMF,
A novel dynamic kinetic resolution accompanied by intramolecular transesterification: Asymmetric synthesis of a 4-hydroxymethyl-2-oxazolidinone from serinol derivatives
Sugiyama, Shigeo,Watanabe, Shoko,Inoue, Takayuki,Kurihara, Rie,Itou, Takahiro,Ishii, Keitaro
, p. 3417 - 3425 (2007/10/03)
Reaction paths of the one-pot reaction of (R)-2-(α-methylbenzyl)amino-1,3-propanediol (1) and 2-chloroethyl chloroformate with DBU giving (4S,αR)-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone [(4S)-2] (94% de) were investigated. Intermediates of this reaction, 2-chloroethyl (2S)- and 2-chloroethyl (2R)-3-hydroxy-2-[(αR)-α-methylbenzyl]aminopropyl carbonates [(2S)-4 and (2R)-4], were synthesized individually. After the addition of DBU to the respective solution of the carbonate (2S)-4 and that of (2R)-4 in dichloromethane, the intramolecular transesterification between (2S)-4 and (2R)-4 and the diastereoselective intramolecular cyclization proceeded to afford (4S)-2 in high diastereomeric excess. Therefore, two monocarbonates (2S)-4 and (2R)-4 were kinetically resolved by this cyclization during the intramolecular transesterification between (2S)-4 and (2R)-4. We found that this process involved dynamic kinetic resolution accompanied by intramolecular transesterification.
One-pot acylation and fractional crystallization: Preparation of optically active serinol monobenzoates
Sugiyama, Shigeo,Inoue, Takayuki,Ishii, Keitaro
, p. 2153 - 2160 (2007/10/03)
Mono-O-acylation of (R)-2-(α-methylbenzyl)amino-1,3-propanediol 1 with 4-nitrobenzoyl chloride and DMAP in dichloromethane at room temperature gave crystals of optically active (2S,αR)-3-hydroxy-2-(α-methylbenzyl)aminopropyl 4-nitrobenzoate hydrochloride
Asymmetric synthesis of the 4-hydroxymethyl-2-oxazolidinone from the serinol derivative and chloroformates
Sugiyama, Shigeo,Watanabe, Shoko,Ishii, Keitaro
, p. 7489 - 7492 (2007/10/03)
Asymmetric desymmetrization of 2-[(αR)-α-methylbenzyl]amino-1,3-propanediol (1) with 2-chloroethyl chloroformate and DBU at room temperature gave optically active (4S)-4-hydroxymethyl-N-[(αR)-α-methylbenzyl]-2-oxazolidinone [(4S)-2] (up to 94% de). This r