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A new efficient enantioselective synthesis of (+)-cis-2-methyl- 4-propyl-1,3-oxathiane, a valuable ingredient for the aroma of passion fruit

✍ Scribed by Patrizia Scafato; Antonella Colangelo; Carlo Rosini

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
101 KB
Volume
21
Category
Article
ISSN
0899-0042

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✦ Synopsis

Abstract

A new simple route to (+)‐cis‐2‐methyl‐4‐propyl‐1,3‐oxathiane**,** the main component responsible of the passion fruit aroma is shown. Such a procedure consists in the sequence of the asymmetric conjugated addition of a thiol to trans‐2‐hexenal/cleavage of sulfide moiety, which allows to prepare, in only two steps, its immediate precursor, (R)‐3‐mercaptohexan‐1‐ol. Various procedures have been investigated for both the steps, using benzyl and tert‐butyl mercaptan as thiols. The best results have been achieved in the addition of benzyl thiol to trans‐2‐hexenal mediated by a proline‐derived organocatalyst, followed by debenzylation with sodium naphthalenide, affording (R)‐3‐mercaptohexan‐1‐ol with 84% e.e. and a yield much higher (32%) than that previously reported (8.5%). Chirality, 2009. © 2008 Wiley‐Liss, Inc.

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