Synthesis of Enantioenriched Secondary and Tertiary Alcohols via Tricarbonylchromium(0) Complexes of Benzyl Allyl Ethers

Allyl ethers of the tricarbonylchromium(0) complexes of benzylic alcohols undergo highly enantioselective benzylic functionalisation using a chiral base/electrophilic quench sequence; the allyl group is readily removed to reveal a hydroxy group as demonstrated in the syntheses of enantioenriched imi...

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Veröffentlicht in:	European Journal of Organic Chemistry 2009-04, Vol.2009 (10), p.1606-1611
Hauptverfasser:	Abecassis, Keren, Gibson, Susan E., Martin‐Fontecha, Mar
Format:	Artikel
Sprache:	eng
Schlagworte:	Alcohols Alkylation Allylic compounds Chemistry Chiral base Chromium Coordination compounds Enantioselectivity Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Inorganic chemistry and origins of life Noncondensed benzenic compounds Organic chemistry Preparations and properties
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Zusammenfassung:	Allyl ethers of the tricarbonylchromium(0) complexes of benzylic alcohols undergo highly enantioselective benzylic functionalisation using a chiral base/electrophilic quench sequence; the allyl group is readily removed to reveal a hydroxy group as demonstrated in the syntheses of enantioenriched imidazole alcohols, a triol and a tertiary alcohol. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) The tricarbonylchromium(0) complexes of benzyl allyl ethers undergo enantioselective deprotonation/alkylation reactions to giveenantioenriched imidazole alcohols, a triol and a tertiary alcohol after removal of the allyl group.
ISSN:	1434-193X 1099-0690
DOI:	10.1002/ejoc.200900007