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Title: Substrate-controlled Michael additions of titanium enolates from chiral α-benzyloxy ketones to conjugated nitroalkenes
Author: Gómez Palomino, Alejandro
Barrio, Adrián
García-Lorente, P.
Romea, Pedro
Urpí Tubella, Fèlix
Font Bardia, Ma. Mercedes
Keywords: Titani
Issue Date: 17-Oct-2017
Publisher: Wiley-VCH
Abstract: Lewis acid-mediated substrate-controlled reactions of the titanium(IV) enolates of chiral a-benzyloxy ketones with conjugated nitroalkenes give the 2,4-anti-4,5-syn Michael adducts in good yields and diastereomeric ratios. The supplementary Lewis acid plays a key role in the outcome of these transformations, probably as a consequence of the formation of bimetallic enolates that increase the reactivity of the enolate and direct the approach of the nitroalkene. Importantly, the most appropriate Lewis acid depends on the electrophilic partner: TiCl4 is the most suitable Lewis acid for b-aryl nitroalkenes while the best results for b-alkyl nitroalkenes are obtained with SnCl4. Finally, the nitro group of the resultant compounds can be converted into the corresponding amino, oxime, and nitrile groups under mild conditions, which permits the synthesis of a variety of enantiomerically pure derivatives with excellent yields.
Note: Versió postprint del document publicat a:
It is part of: European Journal of Organic Chemistry, 2017, vol. 2017, num. 38, p. 5776-5784
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ISSN: 1434-193X
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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