First highly regio- and diastereoselective [3+2] cycloaddition of chiral nonracemic Fischer carbene complexes with azomethine ylides: An enantioselective synthesis of (+)-Rolipram

Chemistry - A European Journal

Volumn 7, Issue 16, 2001, Pages 3533-3544

  Barluenga, José ^a   Fernández Rodríguez, Manuel A ^a   Aguilar, Enrique ^a   Fernández Marí, Félix ^a,b   Salinas, Alejandro ^a,c   Olano, Bernardo ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

^b Asturpharma   (Spain)

^c Asturiana de Aleaciones (Aleastur)   (Spain)

Author keywords

Azomethine ylides; Carbenes; Cycloaddition; Pyrrolidinones; Rolipram

Indexed keywords

ISOMERS; ORGANIC COMPOUNDS; OXIDATION; SYNTHESIS (CHEMICAL);

CYCLOADDITION;

ADDITION REACTIONS;

ALKENYL GROUP; AZOMETHINE YLIDE; CARBENE; MENTHOL; PYRROLIDINE DERIVATIVE; ROLIPRAM;

ARTICLE; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; METHODOLOGY; OXIDATION; STEREOCHEMISTRY;

ANTIDEPRESSIVE AGENTS; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ROLIPRAM; STEREOISOMERISM;

EID: 0035902854     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010817)7:16<3533::AID-CHEM3533>3.0.CO;2-E     Document Type: Article

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112. 20=+21.5 (c=0.97 in MeOH) for the first, second, and third fraction, respectively} and into the BOC-protected compound 13 to be purified by chiral HPLC analysis. The er values observed in these analyses were 97:3 for the first fraction, 95:5 for the second fraction, and 90:10 for the third fraction. From these results, the presence of the NMR-undetected diastereomer after the cycloaddition step is evident.