One‐Pot Silyl Ketene Acetal‐Formation Mukaiyama–Mannich Additions to Imines Mediated by Trimethylsilyl Trifluoro­methanesulfonate. Issue 33 (13th October 2015)

• Record Type: Journal Article
• Authors: Wade Downey, C.; Ingersoll, Jared A.; Glist, Hadleigh M.; Dombrowski, Carolyn M.; Barnett, Adam T.
• Is Part Of: European journal of organic chemistry. Issue 33(2015)
• Page Start: 7287
• Page End: 7291
• Publication Date: 2015-10-13
• Subjects: C–C coupling -- Aniline synthesis -- Cumulenes -- Silyl ketene acetal; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500958
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: In the presence of trimethylsilyl trifluoromethanesulfonate and trialkylamine base, thioesters are readily converted into silyl ketene acetals in situ and undergo Mukaiyama–Mannich addition to N ‐phenylimines in one pot. The silyl triflate appears to play two roles, activating both the thioester and the imine. This process also works well when thioesters are replaced with amides, esters, or ketones. Products are isolated as desilylated anilines without the necessity of a deprotection step. Yields range from 65 to 99 %. Abstract : Thioesters, amides, esters, and ketones undergo conversion to the respective silyl ketene acetals and addition to imines in one pot when treated with trimethylsilyl trifluoromethanesulfonate and trialkylamine.