6533b855fe1ef96bd12b1392
RESEARCH PRODUCT
Relay Catalysis: Enantioselective Synthesis of Cyclic Benzo-Fused Homoallylic Alcohols by Chiral BrOnsted Acid-Catalyzed Allylboration/Ring Closing Metathesis
Lidia HerreraSilvia CatalánElsa RodríguezSantos FusteroRuben LazaroPablo Barriosubject
relay catalysisTandemChemistryEnantioselective synthesisasymmetric catalysisOne-StepGeneral ChemistryCatalysisalcoholsfused-ring systemsCrotylchemistry.chemical_compoundRing-closing metathesisOrganic chemistryBrønsted–Lowry acid–base theoryallylationdescription
Six- and seven-membered benzo-fused cyclic homoallylic alcohols can be readily synthesized by a tandem chiral BrOnsted acid-catalyzed allyl (crotyl)boration/ring closing metathesis sequence performed under orthogonal relay catalysis conditions. Excellent enantio- and diastereoselectivities are obtained in most of the cases. In addition, the parent crotylboration/RCM process is also described. The required substrates, ortho-vinylbenzaldehydes, are readily available in one step from commercially available starting materials. Both catalysts and reactants are also available from commercial suppliers. The reaction shows broad functional group compatibility and is also suitable for heteroaromatic substrates. Substitution at any position of the aromatic ring is tolerated; however, substitution at position 6 results in a substantial drop in enantioselectivity.
year | journal | country | edition | language |
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2013-04-08 |