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Flexible Synthetic Approach to a ( S )‐Norcamphor‐Based Hydroperoxide: An Efficient Oxidant for Asymmetric Sulfoxidations
Author(s) -
Lattanzi Alessandra,
Piccirillo Sandro,
Scettri Arrigo
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500680
Subject(s) - chemistry , chemoselectivity , biocatalysis , organic chemistry , combinatorial chemistry , stereochemistry , catalysis , reaction mechanism
The renewable tertiary ( S )‐norcamphor‐based hydroperoxide 3 has been efficiently obtained by a simple 4‐step route. Remarkably, complete diastereocontrol was observed in the hydroperoxidation step. This oxidant, when used in the Ti‐catalyzed asymmetric sulfoxidation, showed to be as reactive as previously reported hydroperoxide 2 , but more importantly, high chemoselectivity and improved asymmetric induction were achieved. The synthetic approach used offers the opportunity for designing a variety of functionalized and potentially more efficient norcamphor‐based hydroperoxides. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)