Flexible Synthetic Approach to a ( S )‐Norcamphor‐Based Hydroperoxide: An Efficient Oxidant for Asymmetric Sulfoxidations | Zendy

Lattanzi Alessandra | Zendy; Piccirillo Sandro | Zendy; Scettri Arrigo | Zendy

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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)

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