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The Paternò‐Büchi Reaction of 2‐Furylmethanols
Author(s) -
D'Auria Maurizio,
Racioppi Rocco,
Romaniello Gianfranco
Publication year - 2000
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 - 10.1002/1099-0690(200010)2000:19<3265::aid-ejoc3265>3.0.co;2-6
Subject(s) - chemistry , stereoselectivity , regioselectivity , substituent , furan , enantiomer , derivative (finance) , stereochemistry , organic chemistry , catalysis , financial economics , economics
The Paternò‐Büchi reaction between 2‐furylmethanol derivatives and aromatic carbonyl compounds shows good regioselectivity and high stereoselectivity. The regio‐ and stereoselectivity of the reaction can be explained by assuming a role of both the substituent on the 2‐furylmethanol derivative and the hydroxy group in order to favor the approach of the carbonyl group towards a prochiral face of the furan. Electrochemical and kinetic properties of 2‐furylmethanols are in agreement with an electron‐transfer mechanism. The stereoselectivity of the reaction was confirmed using chiral 2‐furylmethanols: These substrates gave the corresponding Paternò‐Büchi adducts with high enantiomeric excess.