One-pot enol silane formation-Mukaiyama Aldol-type addition to dimethyl acetals mediated by TMSOTf

CW Downey, MW Johnson…

Index: Downey, C. Wade; Johnson, Miles W.; Tracy, Kathryn J. Journal of Organic Chemistry, 2008 , vol. 73, # 8 p. 3299 - 3302

Full Text: HTML

Citation Number: 26

Abstract

Various ketones, esters, amides, and thioesters add in high yield to dimethyl acetals in the presence of silyl trifluoromethanesulfonates and an amine base. Acetals derived from aryl, unsaturated, and aliphatic aldehydes are all effective substrates. The reaction proceeds in a single reaction flask, with no purification of the intermediate enol silane necessary.

~75%

~86%

~99%

~89%

Acid catalyzed rearrangement of vinyl and ketene acetals

[Maziarz, Elzbieta; Furman, Bartlomiej Tetrahedron, 2014 , vol. 70, # 8 p. 1651 - 1658]

Rhodium-catalyzed addition of alcohols to terminal enones

[Farnworth, Marc V.; Cross, Michael J.; Louie, Janis Tetrahedron Letters, 2004 , vol. 45, # 40 p. 7441 - 7443]

Platinum??Catalyzed Multi??Step Reaction of Propargyl Alcoho...

[Bhuvaneswari, Sivakolundu; Jeganmohan, Masilamani; Cheng, Chien-Hong Chemistry - An Asian Journal, 2010 , vol. 5, # 1 p. 141 - 146]

SET photochemistry of flavin-cyclopropylamine systems. Model...

[Kim, Jong-Man; Bogdan, Michael A.; Mariano, Patrick S. Journal of the American Chemical Society, 1991 , vol. 113, # 24 p. 9251 - 9257]

Synthesis of. beta.-methoxy enones via a new two-carbon exte...

[Hudlicky, Tomas; Olivo, Horacio F.; Natchus, Michael G. Journal of Organic Chemistry, 1990 , vol. 55, # 15 p. 4767 - 4770]