913288-73-0Relevant academic research and scientific papers
Anti and syn glycolate aldol reactions with a readily displaced thiol auxiliary
Fanjul, Sandra,Hulme, Alison N.
supporting information; experimental part, p. 9788 - 9791 (2009/04/07)
(Chemical Equation Presented) The TBDPS protected glycolate derivative of thiol auxiliary 1 is readily prepared (3 steps, 80% overall yield) and has been shown to give excellent anti:syn selectivity (>97:3) and high facial selectivity (88:12 to 97:3) in g
Achieving high selectivity and facile displacement with a new thiol auxiliary for boron-mediated aldol reactions
Fanjul, Sandra,Hulme, Alison N.,White, John W.
, p. 4219 - 4222 (2007/10/03)
(Chemical Equation Presented) Synthesis of a new thiol auxiliary (1) is readily achieved (in five or six steps, >74% overall yield from norephedrine) and is shown to give high diastereoselectivity in boron-mediated anti-aldol reactions with a range of aldehydes. This new thiol auxiliary may be directly displaced by a range of nucleophiles under very mild conditions, to give the corresponding phosphonate esters, alcohols, acids, SNAC thiolesters, and methyl esters.
