Metallophosphites as Umpolung Catalysts:  The Enantioselective Cross Silyl Benzoin Reaction

• Published in: Journal of the American Chemical Society Vol. 126; no. 10; pp. 3070 - 3071
• Main Authors: Linghu, Xin, Potnick, Justin R, Johnson, Jeffrey S
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 17.03.2004; Amer Chemical Soc
• Subjects: Chemical reactivity; Chemistry; Chemistry, Multidisciplinary; Exact sciences and technology; Organic chemistry; Physical Sciences; Reactivity and mechanisms; Science & Technology; ASYMMETRIC-SYNTHESIS; LIGANDS; ACIDS; BOND FORMATION; CONDENSATION; BROOK REARRANGEMENT; DERIVATIVES; MICHAEL ADDITION; Organic phosphite; Catalytic reaction; Enantioselectivity; Catalyst selectivity; Silicon Organic compounds; Organic silane; Experimental study; Homogeneous catalysis; Asymmetric reaction; Benzenic compound; Catalyst activity; Benzoin condensation; Benzaldehyde derivatives
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja0496468

Carbonyl polarity reversal (umpolung) has been realized employing metallophosphites as catalysts. As a result, nonenzymatic asymmetric cross silyl benzoin reactions have been achieved, giving optically active silyl ether-protected benzoin adducts. The reaction is general with respect to aryl, alkyl, and heterocyclic substrates with good to excellent yields and good to excellent enantioselectivities.