Asymmetric induction by the cholestanic moiety on tropos species: synthesis and stereochemical characterization of bile acid-based biphenyl phosphites.
Three different bile acid-derived biphenyl phosphites were synthesized, starting from cholic and deoxycholic acids and biphenol, and their stereochemical features were checked by CD and NMR spectroscopies. On the basis of the spectroscopic results, the capability of the cholestanic system to induce a prevalent sense of twist on the biphenyl moiety of the bile acid-derived phosphites as well as their tropos nature was inferred.
Iuliano
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A
Dipartimento di Chimica e Chimica Industriale, Università di Pisa, via Risorgimento 35, 56126 Pisa, Italy. iuliano@dcci.unipi.it
Facchetti
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S
Uccello-Barretta
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G