Stereoselective Multiple Bond-Forming Transformations in by Jean Rodriguez, Damien Bonne, Dieter Enders

By Jean Rodriguez, Damien Bonne, Dieter Enders

Combining the $64000 learn subject of a number of bond-forming adjustments with eco-friendly chemistry, this e-book is helping chemists establish contemporary sustainable stereoselective artificial sequences.

•    Combines the $64000 examine subject of a number of bond-forming modifications with eco-friendly chemistry and sustainable development
•    Offers a important source for getting ready compounds with a number of stereogenic facilities, an enormous box for artificial chemists
•    Organizes chapters by means of molecular constitution of ultimate items, making for a handbook-style resource
•    Discusses purposes of the synthesis of average items and of drug intermediates
•    Brings jointly otherwise-scattered information regarding a few key, effective chemical reactions

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Additional info for Stereoselective Multiple Bond-Forming Transformations in Organic Synthesis

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The new bisphosphoric acid 102 derived from the linked BINOL could efficiently promote the proposed threecomponent asymmetric reaction and deliver a series of multiply substituted pyrrolidines 101 in high yields with excellent enantioselectivities under mild conditions [41]. 24 89 91 OH Up to 93% yield, 95:5 dr 90 Diastereoselective synthesis of γ-lactams by a four-component reaction. 25 OtBu 1 R NC 94 CO2Me NOH 97 Co-catalyst R2 O 96 (5 mol%) 97, THF, 4 °C NH2 92 S-R3 O O O R4 R2 N H 95 CN Yield up to 88% endo:exo up to >19:1 dr up to >19:1 ee up to 98% Dynamic one-pot, three-component catalytic asymmetric cycloaddition.

Mechanistically, in the course of these reactions, metalation of an iminoester with a chiral metal complex results in the formation of a well-organized ligand/metal/azomethine ylide complex. In many cases, the intermediate can add to alkenes with high degrees of regio, diastereo, and enantioselectivity by the use of appropriate chiral ligands. 2) have been applied in the 1,3-DC reactions of azomethine ylides with alkenes, and excellent results have been obtained. Lewis acid-catalyzed [3 + 2] cycloadditions of activated donor–acceptor cyclopropanes with aldehydes/ketones are particularly attractive methods for the synthesis of substituted tetrahydrofurans [8].

Construction of enantiopure pyrrolidine ring system via asymmetric[3+2]-cycloaddition of azomethine ylides. Chemical Reviews, 106, 38 FIVE-MEMBERED HETEROCYCLES 4484–4517. (c) Stanley, L. , Sibi, M. P. (2008). Enantioselective copper-catalyzed 1,3-dipolar cycloadditions. Chemical Reviews, 108, 2887–2902. , Wang, W. (2014). Recent advances in organocatalytic asymmetric synthesis of polysubstituted pyrrolidines. Tetrahedron Letters, 55, 784–794. 4. -D. (2006). A highly enantio- and diastereoselective Cu-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with nitroalkenes.

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