Get Stereoselective Formation of Amines PDF

By Wei Li, Xumu Zhang

ISBN-10: 3642539289

ISBN-13: 9783642539282

ISBN-10: 3642539297

ISBN-13: 9783642539299

Each assessment in the quantity seriously surveys one point of that subject and areas it in the context of the quantity as an entire. the main major advancements of the final five to ten years are awarded utilizing chosen examples to demonstrate the rules mentioned. The assurance isn't really meant to be an exhaustive precis of the sector or comprise huge amounts of information, yet should still otherwise be conceptual, targeting the methodological pondering that might let the non-specialist reader to appreciate the data awarded. Contributions additionally provide an outlook on capability destiny advancements within the field.

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Schaum R (1998) PhD Thesis, Universite´ de Montreal, Montreal, Canada 143. Torrente S, Alonso R (2001) Org Lett 3:1985–1987 144. Miyabe H, Yamaoka Y, Takemoto Y (2005) J Org Chem 70:3324–3327 145. Ramon DJ, Yus M (2004) Curr Org Chem 8:149–183 146. Obrecht D, Bohdal U, Broger C, Bur D, Lehmann C, Ruffieux R, Scho¨nholzer P, Spiegler C, Mu¨ller K (1995) Helv Chim Acta 78:563–580 147. Enders D (1984) In: Morrison JD (ed) Asymmetric synthesis. Academic, New York 148. Husson H-P, Royer J (1999) Chem Soc Rev 28:383–394 149.

B. Charette (*) and V. B. Charette and V. Lindsay Fig. 1 Most common approaches to α-chiral amines 1 Introduction The ubiquity of α-chiral amines in bioactive molecules and natural products has been a constant source of inspiration for the development of new and more effective methods for their formation. Various approaches to α-chiral amines are shown in Fig. 1. Common approaches to generate α-chiral amines include imine reduction [1] and Strecker [2] and Mannich type (aza-Henry) reactions [3, 4].

In analogy to the extensively studied addition of nucleophiles to carbonyl substrates, the predictive Cram, Felkin–Ahn, and Cornforth models are also applicable to imine chemistry. Thus in principle a non-chelating chiral group at the α-position of the acyclic imine will afford the Felkin–Ahn product issued from minimization of torsional strain at the transition state and subsequent attack on the most accessible face of the imine (Fig. 5a). Conversely, the presence of a chelating functionality at this position leads to the product issued from the addition on the least hindered face of the chelate intermediate according to Cram’s cyclic model, under the appropriate reaction conditions favoring the formation of such chelate (Fig.

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Stereoselective Formation of Amines by Wei Li, Xumu Zhang


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