1191944-96-3Relevant academic research and scientific papers
Enantio- and diastereoselective synthesis of (E)-1,5-syn-diols: Application to the synthesis of the C(23)-C(40) fragment of tetrafibricin
Kister, Jeremy,Nuhant, Philippe,Lira, Ricardo,Sorg, Achim,Roush, William R.
supporting information; scheme or table, p. 1868 - 1871 (2011/06/22)
A highly stereoselective synthesis of (E)-1,5-syn-diols 6 is described. The kinetically controlled hydroboration of allenyltrifluoroborate 8 with Soderquist borane 2 provides the (Z)-allylic trifluoroborate 9, which undergoes sequential allylboration with two different aldehydes to provide (E)-1,5-syn-diols 6 in 72-98% yields with >95% ee and >20:1 dr. Application of this method to the synthesis of the tetrafibricin C(23)-C(40) fragment 19 is described.
Stereoselective synthesis of γ-substituted (Z)-allylic boranes via kinetically controlled hydroboration of allenes with 10-TMS-9-borabicyclo[3.3.2] decane
Kister, Jeremy,DeBaillie, Amy C.,Lira, Ricardo,Roush, William R.
supporting information; experimental part, p. 14174 - 14175 (2010/02/16)
(Chemical Equation Presented) Kinetically controlled hydroboration of allenes 8 and 14a-d with the readily accessible Soderquist borane 7, which is generated in situ from borohydride 6, constitutes a convenient and preparatively useful method for synthesi
