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Chiral o ‐Methoxyaryldiazaphosphonamides − A New Class of Efficient Lewis Bases in the Catalytic Asymmetric Ring Opening of Cyclooctene Oxide with Silicon Tetrachloride
Author(s) -
Buono Gérard
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(20021)2002:1<218::aid-ejoc218>3.0.co;2-#
Subject(s) - cyclooctene , chemistry , silicon tetrachloride , catalysis , ring (chemistry) , lewis acids and bases , silicon , oxide , organic chemistry , polymer chemistry
This paper reported a new class of diastereomerically pure ortho ‐methoxydiazaphosphonamide Lewis bases prepared from the corresponding o ‐hydroxyarylphosphonamides. These bases have been applied to the catalytic asymmetric ring opening of cyclooctene oxide with SiCl 4 . During the last weeks, I disclosed in a correspondence (corrigenda) to Angewandte Chemie that I personally could not reproduce results previously published in this journal about the opening of cyclooctene oxide by such Lewis base catalysts.1 Instead, I obtained results similar to those reported by Denmark et al. in their rebuttal of our original communication.2,3 To date, my co‐workers4 have been unable to provide an appropriate scientific rationale for the non‐reproducibility of the former results and several inconsistencies I found in analytical data they provided me with. Consequently, all the material concerning asymmetric catalysis in the paper previously published in this journal should be considered as irrelevant. Therefore, I wish to withdraw this article.