TY - JOUR T1 - Highly enantioselective synthesis of gamma-nitro heteroaromatic ketones in a doubly stereocontrolled manner catalyzed by bifunctional thiourea catalysts based on dehydroabietic amine: a doubly stereocontrolled approach to pyrrolidine carboxylic acids. AU - Jiang,Xianxing, AU - Zhang,Yifu, AU - Chan,Albert S C, AU - Wang,Rui, PY - 2008/12/11/pubmed PY - 2009/2/12/medline PY - 2008/12/11/entrez SP - 153 EP - 6 JF - Organic letters JO - Org Lett VL - 11 IS - 1 N2 - A new class of dehydroabietic amine-substituted primary amine-thiourea bifunctional catalysts were designed and synthesized. The doubly stereocontrolled organocatalytic conjugate addition of a variety of heterocycles-bearing ketones to nitroalkenes was investigated for the first time, affording (S)- or (R)-gamma-nitro heteroaromatic ketones with excellent enantioselectivities (up to ee >99%). Furthermore, the nearly optically pure gamma-nitro heteroaromatic ketones can be readily transformed into chiral pyrrolidine carboxylic acids. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19067569/Highly_enantioselective_synthesis_of_gamma_nitro_heteroaromatic_ketones_in_a_doubly_stereocontrolled_manner_catalyzed_by_bifunctional_thiourea_catalysts_based_on_dehydroabietic_amine:_a_doubly_stereocontrolled_approach_to_pyrrolidine_carboxylic_acids_ L2 - https://doi.org/10.1021/ol8025268 DB - PRIME DP - Unbound Medicine ER -