Synthesis of enantiomerically pure (R)- and (S)-2-ethoxycarbonylmethyl- 2-hydroxy-cyclohexanones

Tetrahedron Asymmetry

Volumn 9, Issue 19, 1998, Pages 3445-3453

  García Ruano, José L ^a   Barros, David ^a   Maestro, M Carmen ^a   Alcudia, Ana ^b   Fernández, Inmaculada ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

2 ETHOXYCARBONYLMETHYL 2 HYDROXYCYLOHEXANONE; ACETIC ACID ETHYL ESTER; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032476175     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00367-X     Document Type: Article

References (21)

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18. 13C NMR spectrum of compound 4 did not allow us to differentiate between a thioketal or a thioketal S-oxide structure.
19. The nucleophilic attack of the thiolate (disulfide leaving group), to a β-ketosulfide has been previously reported (see Ref. 9).
20. LHMDS was preferred as the base used in enolate generation, to prevent a possible attack of the amine to the monothioketal S-oxide.
21. 3 was necessary to observe completely separated signals of the ester ethoxy group.