Tamed by chelation: The MgBr 2 chelation of prochiral malonaldehydes allows diastereoselective monoaddition reactions with allyl stannane nucleophiles (see scheme; PG=protecting group, TBDMS=tert- butyldiphenylmethylsilyl, Tr=trityl). In the same pot, addition of a second nucleophile proceeds in high diastereoselectivity to generate nonsymmetric products with up to five contiguous stereogenic centers, including a chiral all-carbon quaternary center.
Linclau, B., Cini, E., Oakes, C.S., Josse, S., Light, M., Ironmonger, V. (2012). Stereoarrays with an all-carbon quaternary center: Diastereoselective desymmetrization of prochiral malonaldehydes. ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, 51(5), 1232-1235 [10.1002/anie.201107370].
Stereoarrays with an all-carbon quaternary center: Diastereoselective desymmetrization of prochiral malonaldehydes
Cini, ElenaMembro del Collaboration Group
;
2012-01-01
Abstract
Tamed by chelation: The MgBr 2 chelation of prochiral malonaldehydes allows diastereoselective monoaddition reactions with allyl stannane nucleophiles (see scheme; PG=protecting group, TBDMS=tert- butyldiphenylmethylsilyl, Tr=trityl). In the same pot, addition of a second nucleophile proceeds in high diastereoselectivity to generate nonsymmetric products with up to five contiguous stereogenic centers, including a chiral all-carbon quaternary center.File | Dimensione | Formato | |
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https://hdl.handle.net/11365/1077906