Non-enzymatic diastereoselective asymmetric desymmetrization of 2-benzylserinols giving optically active 4-benzyl-4-hydroxymethyl-2- oxazolidinones: Asymmetric syntheses of α-(hydroxymethyl)phenylalanine, N-Boc-α-methylphenylalanine, cericlamine and BIRT-377

Tetrahedron

Volumn 68, Issue 38, 2012, Pages 8033-8045

  Sugiyama, Shigeo ^a   Arai, Satoshi ^a   Ishii, Keitaro ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Asymmetric desymmetrization; Cyclic carbonate; Debenzylation; Fractional crystallization; Oxazolidinone; Serinol

Indexed keywords

(4 BENZYL 2 OXAZOLIDINON 4 YL)METHYL 4 TOLUENESULFONATE; (4 BENZYL 2 OXO 4 OXAZOLIDINE)CARBOXYLIC ACID; 2 (4 BROMOBENZYL 2 (ALPHA METHYLBENZYL)AMINO 1,3 PROPANEDIOL; 2 BENZYL 2 (ALPHA METHYLBENZYL)AMINO 1,3 PROPANEDIOL; 2 BENZYLSERINOL DERIVATIVE; 2 DICHLOROBENZYL 2 (ALPHA METHYLBENZYL)AMINO 1,3 PROPANEDIOL; 4 (3,4 DICHLOROBENZYL) 4 HYDROXYMETHYL 3 (ALPHA METHYLBENZYL) 2 OXAZOLIDINONE; 4 (4 BROMOBENZYL) 4 HYDROXYMETHYL 3 (ALPHA METHYLBENZYL) 2 OXAZOLIDINONE; 4 BENZYL 2 OXO OXAZOLIDINON 4 YLMETHYL 4 TOLUENE 4 SULFONATE; 4 BENZYL 2 OXO OXAZOLIDINON 4 YLMETHYL METHANESULFONATE; 4 BENZYL 3 (ALPHA METHYLBENZYL) 2 OXO OXAZOLIDINON 4 YLMETHYL 4 TOLUENE 4 SULFONATE; 4 BENZYL 3 (ALPHA METHYLBENZYL) 2 OXO OXAZOLIDINON 4 YLMETHYL METHANESULFONATE; 4 BENZYL 4 HYDROXYMETHYL 2 OXAZOLIDINONE; 4 BENZYL 4 HYDROXYMETHYL 2 OXAZOLIDINONE DERIVATIVE; 4 BENZYL 4 HYDROXYMETHYL 3 (ALPHA METHYLBENZYL) 2 OXAZOLIDINONE; [4 (3,4 DICHLOROBENZYL) 2 OXAZOLIDINON 4 YL]METHYL 4 TOLUENESULFONATE; [4 (4 BROMOBENZYL) 2 OXAZOLIDINON 4 YL]METHYL 4 TOLUENESULFONATE; ALPHA (HYDROXYMETHYL)PHENYLALANINE; BENZENE DERIVATIVE; BIRT 377; BROMINE DERIVATIVE; CERICLAMINE; DIETHYL 2 (3,4 DICHLOROBENZYL) 2 (ALPHA METHYLBENZYL)AMINOMALONATE; DIETHYL 2 (4 BROMOBENZYL) 2 (ALPHA METHYLBENZYL)AMINOMALONATE; DIETHYL 2 BENZYL N (ALPHA METHYLBENZYL)AMINOMALONATE; N BOC ALPHA METHYLPHENYLALANINE; OXAZOLIDINONE DERIVATIVE; PHENYLALANINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ADDITION REACTION; ANALYTIC METHOD; ARTICLE; DEBENZYLATION; DRUG SYNTHESIS; NONENZYMATIC DIASTEREOSELECTIVE ASYMMETRIC DESYMMETRIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 84864631592     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.06.090     Document Type: Article

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