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Absolute Configuration of 3‐Substituted 1‐Azabicyclo[2.2.1]heptanes
Author(s) -
Boelsterli Jakob,
Eggnauer Ursula,
PomboVillar Esteban,
Weber HansPeter,
Walkinshaw Malcolm,
Gould Robert O.
Publication year - 1992
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19920750210
Subject(s) - chemistry , absolute configuration , enantiomer , heptane , derivative (finance) , tartrate , stereochemistry , single crystal , crystallography , organic chemistry , financial economics , economics
The l‐azabicyclo[2.2.1]heptan‐3‐ exo ‐ol ( 2 ) was resolved by fractional crystallisation of its hydrogen tartrate salts. The enantiomers (+)‐ and (−)‐ 2 were oxidised to the ketones (−)‐ 4 and (+)‐ 4 , respectively ( Scheme ). CD spectroscopy suggested that (−)‐ 4 possesses the (1 R ,4 S )‐configuration. This absolute configuration was confirmed by single‐crystal X‐ray diffraction of the derivative (+)‐(1 R ,4 R )‐3‐(1,3‐dithian‐2‐ylidene)‐1‐azabicyclo [2.2.1]‐heptane ((+)‐ 5 ).