862735-86-2Relevant academic research and scientific papers
A convenient multigram synthesis of highly enantioenriched methyl 3-silylglycidates
Lowe, Jason T.,Youngsaye, Willmen,Panek, James S.
, p. 3639 - 3642 (2007/10/03)
A multigram scale synthesis of the four stereoisomers of methyl 3-silylglycidates (epoxysilanes) with high enantiopurity is described. Key reactions include a Sharpless asymmetric epoxidation (SAE) of a trans-vinylsilane and an enzymatic resolution of a r
Synthesis and [4 + 2]-annulation of enantioenriched (Z)-crotylsilanes: Preparation of the C1-C13 fragment of bistramide A
Lowe, Jason T.,Panek, James S.
, p. 3231 - 3234 (2007/10/03)
(Chemical Equation Presented) New chiral crotylsilanes that bear a (Z)-olefin geometry were synthesized in high enantiopurity. The reagents participate in [4 + 2]-annulations with aldehydes to give stereochemically complementary pyrans (relative to (E)-crotylsilanes) bearing 2,6-cis-5,6-cis and 2,6-trans-5,6-cis relationships of peripheral functionalities. A stereoselective synthesis of the C1-C13 fragment of bistramide A is also described highlighting this annulation strategy.
