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By Herbert Waldmann

Like its predecessor, natural Synthesis Highlights II surveys fresh accomplishments and present developments in man made natural chemistry. half I describes new tools and reagents together with uneven carbon-carbon bond formation with metallocenes and with enzymes, through transitority silicon connections, and by way of carbohydrate complexes. half II describes landmarks within the synthesis of typical items and surveys artificial innovations to assorted sessions of normal items. The 40 essays during this quantity undergo witness to the creativity and ability that have ended in the hot advances within the box. either complicated scholars and researchers energetic within the box will welcome this as a resource of rules and idea.

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By Herbert Waldmann

Like its predecessor, natural Synthesis Highlights II surveys fresh accomplishments and present developments in man made natural chemistry. half I describes new tools and reagents together with uneven carbon-carbon bond formation with metallocenes and with enzymes, through transitority silicon connections, and by way of carbohydrate complexes. half II describes landmarks within the synthesis of typical items and surveys artificial innovations to assorted sessions of normal items. The 40 essays during this quantity undergo witness to the creativity and ability that have ended in the hot advances within the box. either complicated scholars and researchers energetic within the box will welcome this as a resource of rules and idea.

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H. Heathcock, M. C. H. Lampe, Tetrahedron 1981,37,4087. [17] R. 0. Herold, S. Wyler-Helfer, M. Riediker, Helv. Chim. Actu 1990, 73,659. O. Riediker,Angew. Chem. 1989,101, 491; Angew. Chem. Int. Ed. Engl. 1989,28,497. [19] M. Piantini, G. Togni, Angew. Chem. 1989, 101, 493; Angew. Chem. Int. Ed. Engl. 1989,28, 499. Organic Synthesis Highlights I1 Edited by Herbert Waldmann OVCH Verlagsgesellschafi mbH,1995 Asymmetric Aza-Diels-Alder Reactions Herbert Waldmann Hetero-Diels-Alder reactions with azasubstituted dienes or dienophiles are powerful methods for the regio- and stereoselective synthesis of nitrogen heterocycles [l] and can play pivotal roles in the construction of many natural products and biologically active compounds.

Thus, with the respective 4-bromophenyl or the 4-N02nes (34) with appreciable diastereomeric phenyl analogue and (S)-1-phenylpropylamine the diastereomers are formed in a ratio ratios. [5] Recently, highly diastereoselective Lewis of ca. 1:l. [7g] If amino acid esters are acid mediated ma-Diels-Alder cycloadditions employed as mediators of selectivity isomer with chiral imines and dienes carrying a chiral ratios up to 93:7 are reached (Scheme 4). auxiliary have also been reported. [6] In these [ 7 k ] This enhanced level of stereodiscrimprocesses 2-amino-1,3-butadienes embodying ination can be explained by the assumption 2-(methoxymethy1)pyrrolidine as mediator of that in these cases in the aqueous medium highly ordered transition states (40), with minchirality were employed with great success.

This is attacked at the cation by the carbonyl group of the chiral a-hydroxy ester. Thereby the proton would be transferred perpendicular to the double blond to the acarbon of the enolate. Rebek et al. investigated the tricyclic lactams (53) and (54), which can be obtained from Kemp's triacid and chiral alkylarylamines by diastereomer separation, as proton sources in this transformation. [171 For aromatic a-hydroxycarboxylic acid esters only unreproducible results were obtained, but the alkylsubstituted intermediates (50) were protonated with high selectivity.

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