Two complementary approaches to methyl 5-alkyltetra- mate derivatives

March 08, 2024

• Title:       

  Two complementary approaches to methyl 5-alkyltetra-mate derivatives 

• Image Source:

  A flexible approach to methyl (5S)-5-alkyltetramate derivatives

• Mark:

  Scheme 1

• Associated context:

  In view of SAR study, more flexible methods would be those allowing a flexible and direct introduction of substituent at the C-5 position of a tetramate derivative. Recently, several carbanionic approaches based on intermediates such as A have been reported (Scheme 1).²³ In this regard, we have reported two flexible approaches to (S)-5-alkyl- tetramic acid^24a and methyl (R)-5-alkyltetramate^24b derivatives. As a continuation of our studies in this area, we now report a complementary yet flexible carbocationic synthon B based approach²⁵ to methyl 5-alkyltetramate  derivatives 6 using (S)-phenylglycinol as a chiral auxiliary.