Rationally designed chiral enol borinates: Powerful reagents for the stereoselective synthesis of natural products
Articolo
Data di Pubblicazione:
1997
Citazione:
Rationally designed chiral enol borinates: Powerful reagents for the stereoselective synthesis of natural products / C.M.A. Gennari. - In: PURE AND APPLIED CHEMISTRY. - ISSN 0033-4545. - 69:3(1997), pp. 507-512. [10.1351/pac199769030507]
Abstract:
We recently described the development of a quantitative transition state model for the prediction of stereoselectivity in the boron-mediated aldol reaction. This model provides qualitative insights into the factors contributing to the stereochemical outcome of a variety of reactions of synthetic importance. The force field model was used to assist the design and preparation of new chiral boron ligands derived from menthone. The chiral boron enolates were used in various stereoselective processes, including the addition to chiral aldehydes and the reagent-controlled total synthesis of (3S,4S)-statine. The chiral enolates derived from alpha-halo and alpha-oxysubstituted thioacetates were added to aldehydes and imines. Addition to imines leads to the enantioselective synthesis of chiral aziridines, a formal total synthesis of (+)thiamphenicol, and a new highly efficient synthesis of the paclitaxel (taxol(R)) C-13 side-chain and taxol semisynthesis from baccatin III. The stereochemical outcome of the addition to imines was rationalised with the aid of computational studies.
Tipologia IRIS:
01 - Articolo su periodico
Elenco autori:
C.M.A. Gennari
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