Using (S)-prolinol as a chiral auxiliary, axially chiral vinylallenes with excellent enantiopurity (up to >99% enantiomeric excess (ee)) were readily prepared from optically pure propargylamines in the presence of AgNO 3 under microwave irradiation. Subsequent (hetero)-Diels−Alder reaction of these axially chiral vinylallenes with azodicarboxylates or maleimides on water demonstrates excellent axial-to-point chirality transfer (up to 99% ee).
Stereoselective Intramolecular Carbene C-H Insertion Catalyzed by Rhodium(III) Porphyrin Complexes. -Among some Rh(III)-porphyrin complexes tested, (I) is found to be the most efficient catalyst for the intramolecular carbene C-H insertion of α-diazoacetamides to form βor γ-lactams with high diastereoselectivity. -(LO, V. K.-Y.; THU, H.-Y.; CHAN, Y.-M.; LAM, T.-L.; YU, W.-Y.; CHE*, C.-M.; Synlett 2012, 19, 2753-2757, http://dx.
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