Relay Catalysis: Enantioselective Synthesis of Cyclic Benzo-Fused Homoallylic Alcohols by Chiral Brønsted Acid-Catalyzed Allylboration/Ring Closing Metathesis

Six‐ and seven‐membered benzo‐fused cyclic homoallylic alcohols can be readily synthesized by a tandem chiral Brønsted acid‐catalyzed allyl (crotyl)boration/ring closing metathesis sequence performed under orthogonal relay catalysis conditions. Excellent enantio‐ and diastereoselectivities are obtai...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2013-04, Vol.355 (6), p.1058-1064
Main Authors: Fustero, Santos, Rodríguez, Elsa, Lázaro, Rubén, Herrera, Lidia, Catalán, Silvia, Barrio, Pablo
Format: Article
Language:English
Subjects:
alcohols
allylation
asymmetric catalysis
fused-ring systems
relay catalysis
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Summary:Six‐ and seven‐membered benzo‐fused cyclic homoallylic alcohols can be readily synthesized by a tandem chiral Brønsted 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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201201095