ChemInform Abstract: Use of N‐Methylformamide as a Solvent in Indium‐Promoted Barbier Reactions en Route to Enediyne and Epoxy Diyne Formation: Comparison of Rate and Stereoselectivity in C—C Bond‐Forming Reactions with Water.

Abstract

Alkynes P 0027Use of N-Methylformamide as a Solvent in Indium-Promoted Barbier Reactions en Route to Enediyne and Epoxy Diyne Formation: Comparison of Rate and Stereoselectivity in C-C Bond-Forming Reactions with Water. -It is found that the Barbier reaction of the aldehydes (I) with the sulfide (II) in N-methylformamide solution proceeds faster and with higher stereoselectivity than in water. In the presence of InCl3, the syn-adducts are mainly formed whereas without InCl3 the anti-products are predominantly obtained. Subsequent treatment with TosOH or Me 3 OBF 4 allows a new and facile access to enediynes and epoxydiynes. -(FRIMPONG, K.; WZOREK, J.; LAWLOR, C.; SPENCER, K.; MITZEL*, T.; J. Org. Chem. 74 (2009) 16, 5861-5870; Dep. Chem., Trinity Coll., Hartford, CT 06106, USA; Eng.) -Jannicke 52-060