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A New and Convenient Route to Optically Active 2‐Phosphoryl‐3‐oxo‐5‐alkyl/‐aryltetrahydrofurans and Their Reactions
Author(s) -
Xu Chengfu,
Zhang Yonghui,
Yuan Chengye
Publication year - 2004
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/ejoc.200400018
Subject(s) - chemistry , alkyl , enantiomer , intramolecular force , aryl , substrate (aquarium) , rhodium , optically active , stereochemistry , medicinal chemistry , organic chemistry , catalysis , oceanography , geology
Abstract The two enantiomers of 4‐hydroxy‐2‐oxo‐4‐alkyl/‐arylalkylphosphonates were prepared chemoenzymatically and converted to chiral 2‐phosphoryl‐3‐oxo‐5‐alkyl/‐aryl tetrahydrofurans using an intramolecular O−H insertion reaction catalyzed by rhodium( II ) acetate. The potential biological activity of the resulting tetrahydrofurans is of much interest. The presence of the β‐ketophosphonate skeleton in these heterocycles allowed their use as substrate in the cyclic Horner−Wadsworth−Emmons reaction with aldehydes or ketones furnishing chiral α,β‐unsaturated ketones − a new class of building block in organic synthesis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)