Efficient radical cyclisation of secondary amides: An enantioselective synthesis of phenyl allokainoid

Tetrahedron Letters

Volumn 40, Issue 17, 1999, Pages 3487-3490

  Bryans, Justin S ^b   Large, Jonathan M ^a   Parsons, Andrew F ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Cyclisation; Kainoids; Radicals and radical reactions; Tin and compounds

Indexed keywords

AMIDE; KAINIC ACID DERIVATIVE; PHENYL GROUP; PYRROLIDINE DERIVATIVE; RADICAL; SERINE DERIVATIVE; TRIBUTYLTIN;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; RACEMIC MIXTURE; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033597376     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00431-1     Document Type: Article

References (22)

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15. 10. This can be compared to the cyclisation of a similar N-benzyl substituted precursor, which gave a 1:1:1 mixture of pyrrolidinone diastereoisomers. Parsons, A.F.; Taylor, R.J.K. J. Chem. Soc., Perkin Trans, 1, 1994, 1945-1951.
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21. 13. Tin-mediated cyclisations were carried out using 0.2-1.8 mmol of (15) and some reactions gave acyclic product, derived from simple reduction, in low yield (maximum 8%).
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