Journal of the American Chemical Society p. 8776 - 8782 (1999)
Update date:2022-09-26
Topics:
Barluenga, Jose
Rodriguez, Felix
Vadecard, Jerome
Bendix, Maximilian
Fananas, Francisco J.
Lopez-Ortiz, Fernando
Rodriguez, Miguel A.
In-situ-generated dialkylboroxy and diaminoboroxy Fischer carbene complexes lead to oxaborolane or oxazaborolidine derivatives via an intramolecular C-H insertion reaction. Further oxidation of these intermediates yields 1,3-diol or 1,2-amino alcohol derivatives. Diastereoselectivities as high as 99% are reached when starting from boroxy Fischer carbene complexes derived from terpenes, which represents a regio-and diastereoselective modification of this type of natural product. The influence of the Cβ substituents relative to the boron atom on the reaction path is studied, and a mechanism is proposed after identification of an intermediate by NMR. In addition, theoretical calculations show the presence of a boron-metal interaction, which could result as key step to the C-H insertion reaction.
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Doi:10.1021/bi00835a055
(1969)Doi:10.1021/jo9605814
(1996)Doi:10.1021/ja01207a038
(1946)Doi:10.1007/BF02494755
(1999)Doi:10.1021/jm9605593
(1997)Doi:10.1016/0968-0896(96)00094-6
(1996)