Highly enantioselective synthesis of substituted piperidines using the chiral lithium amide base approach

Synlett

Volumn , Issue 8, 1999, Pages 1292-1294

  Goldspink, Nicholas J ^a   Simpkins, Nigel S ^a   Beckmann, Marion ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Asymmetric synthesis; Chiral lithium amide

Indexed keywords

AMINE; HETEROCYCLIC COMPOUND; LITHIUM DERIVATIVE; PIPERIDINE DERIVATIVE;

ALKYLATION; ARTICLE; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; SYNTHESIS;

EID: 0032792533     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2813     Document Type: Article

References (20)

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10. 4 requires M+W, 382.2019). The enantiomeric excess was determined by HPLC analysis using a Chiralcel OD column with 1% i-PrOH in hexane as eluant, using UV detection at 254 nm. Retention times were 15.1 min (minor) and 16.5 min (major).
11. The relative and absolute configuration shown for 10 has been proved by X-ray crystallography for 10b, full details will be published elsewhere.
12. The enantiomeric excess has been measured for 10a, 10c and 10e, the other examples are expected to have the same ee.
13. Reaction with benzaldehyde gave three aldol products in a roughly 2:1:2 ratio, whereas the corresponding reactions involving either acetaldehyde or isobutyraldehyde gave single diastereomeric aldolproducts (after chromatography) in modest yield (ca. 40%). Thestereochemistry of these aldol products has not been assigned.
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