Z- and E-selective Horner–Wadsworth–Emmons reactions. Issue 13 (3rd July 2017)

• Record Type: Journal Article
• Authors: Molnár, Katalin; Takács, László; Kádár, Mihály; Faigl, Ferenc; Kardos, Zsuzsanna
• Is Part Of: Synthetic communications. Volume 47:Issue 13(2017)
• Page Start: 1214
• Page End: 1224
• Publication Date: 2017-07-03
• Subjects: Bis(trifluoroethyl) phosphonates -- Horner–Wadsworth–Emmons reaction -- stereoselectivity -- α, β-unsaturated ketones; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2017.1319487
• Languages: English
• ISSNs: 0039-7911

Abstract

ABSTRACT: In the present work, we determined and evaluated the stereochemical outcome of the Horner–Wadsworth–Emmons (HWE) reaction of 2-oxoalkylphosphonates with different ester functions (bis(2, 2, 2-trifluoroethyl), 2, 2, 2-trifluoroethyl methyl, dimethyl) and side chains (aliphatic, aromatic) with three different aldehydes (benzaldehyde, THP- and PPB-protected Corey aldehydes) under two reaction conditions. The " trans " protocol is generally used in the E -selective HWE reactions, while " cis " protocol promotes the Z -selectivity. GRAPHICAL ABSTRACT: