5-Pyrrolidin-2-yltetrazole: A New, Catalytic, More Soluble Alternative to Proline in an Organocatalytic Asymmetric Mannich-type Reaction

Synlett

Volumn , Issue 3, 2004, Pages 558-560

  Cobb, Alexander J A ^a   Shaw, David M ^a   Ley, Steven V ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Asymmetric; Mannich; Organocatalysis; Proline; Tetrazole

Indexed keywords

5 PYRROLIDIN 2 YLTETRAZOLE; ACETONE; CYCLOHEXANONE; KETONE; LACTONE; OXALIC ACID DERIVATIVE; PROLINE; SOLVENT; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG SOLUBILITY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; HYDROLYSIS; MANNICH REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION OPTIMIZATION; SEGREGATION ANALYSIS;

EID: 1442286542     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-817745     Document Type: Article

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24. R(major) = 57 min. For retention times of 2, 4 and 8 see ref. 5a
25. In order to obtain separation on HPLC, the aldehyde was converted to the lactone by reduction with sodium borohydride (Scheme 3) before chromatography to avoid epimerization. This represents a good route to enantiopure functionalized 1-amino-2-alkyl-δ-lactones.