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A Wittig Reaction with 2‐Furyl Substituents at the Phosphorus Atom: Improved ( Z ) Selectivity and Isolation of a Stable Oxaphosphetane Intermediate
Author(s) -
Appel Marco,
Blaurock Steffen,
Berger Stefan
Publication year - 2002
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(200204)2002:7<1143::aid-ejoc1143>3.0.co;2-g
Subject(s) - chemistry , wittig reaction , selectivity , alkene , phosphorus , medicinal chemistry , crystal structure , nuclear magnetic resonance spectroscopy , protecting group , stereochemistry , atom (system on chip) , organic chemistry , catalysis , alkyl , computer science , embedded system
Wittig reactions with ylides bearing one, two or three 2‐furyl groups directly bound to the phosphorus atom have been studied. Greatly improved ( Z )‐alkene selectivities of up to 98:2 could be observed if 2‐furyl groups were present. Monitoring of the reactions by NMR spectroscopy revealed only oxaphosphetane intermediates, which became more stable with increasing number of 2‐furyl substituents bound to the phosphorus atom. Oxaphosphetane 10d , with three furyl groups, was successfully isolated, and the results of a crystal structure analysis are presented. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)