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Synfacts 2008(8): 0872-0872
DOI: 10.1055/s-2008-1078545
DOI: 10.1055/s-2008-1078545
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Catalytic aza-Wittig Cyclization
S.P. Marsden*, A. E. McGonagle, B. McKeever-Abbas
University of Leeds and AstraZeneca Process R&D, Macclesfield, UK
Further Information
Publication History
Publication Date:
23 July 2008 (online)
Significance
The authors report examples of phenanthridine 1 and benzoxazole 2 synthesis by iminophosphorane generation followed by intramolecular aza-Wittig cyclization catalyzed by commercially available phospholene oxide 3. Both azine and azole heterocycles have been synthesized in moderate to good yields (30-87%yield) with attractively low catalyst loadings down to 1 mol%. Furthermore, the use of carboxylic acid derived isocyanates offers a novel disconnection for the synthesis of (benz)oxazoles.