Asymmetric Synthesis of Nitrogen Heterocycles by Jacques Royer, H. P. Husson

By Jacques Royer, H. P. Husson

The following, all points of the subject are awarded in a compact demeanour. The ebook is obviously established, and divided into sections -- uneven synthesis of heterocycles containing just one nitrogen and that of these with multiple nitrogen as a heteroatom -- such that the required details could be stumbled on at a look. The foreign crew of authors presents very important experimental systems, together with business applications.Essential for man made chemists in pharmaceutical and agrochemical chemistry.

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2 cis de 41% trans de > 85% R* = Ph On the other hand, camphorsultam-derived α-bromoenolates reacted with N-Dpp-imine to afford a single cis diastereoisomer in high yield. Removal of the chiral auxiliary was simply performed with LiOH at room temperature. The method was successfully applied to aromatic, para-substituted aromatic, unsaturated, and aliphatic enolates. The introduction of an ortho substituent into the aromatic ring determined the stereoselectivity inversion, often giving exclusively trans products [52].

Schirmeister, T. (1999) Biopolymers, 51, 87. Stapley, E. , Miller, A. , Hernandez, S. and Mata, J. M. (1971) J. , 24, 42–47. Molinski, T. F. and Ireland, C. M. (1988) J. Org. , 53, 2103–5. Gabriel, S. (1888) Chem. , 21, 1049. , Gentilucci, L. and Tolomelli, A. (2003) Aldrichimica Acta, 36, 39–50; (b) Lee, W. K. and Ha, H. J. (2003) Aldrichimica Acta, 36, 57–63; (c) McCoull, W. and Davis, F. A. (2000) Synthesis, 10, 1347–65; (d) Kulkarni, Y. S. (1999) Aldrichimica Acta, 32, 18–27; (e) Padwa, A. (1991) Comprehensive Organic Synthesis, (eds B.

Although cis-aziridines were obtained only in modest yields (5–65%) and stereoselectivities (2–67% ee), a deep exploration of the reaction mechanism allowed to suggest the generation of a transient bis(dihydrooxazole)copper carbene complex that reacts with the imine to form a 21 22 1 Asymmetric Synthesis of Three- and Four-Membered Ring Heterocycles metal-complexed azomethine ylide. This intermediate may undergo intramolecular ring closure to optically active aziridine or it may dissociate to free azomethine ylide, precursor of the formation of racemic aziridine.

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