1191944-98-5Relevant academic research and scientific papers
Development of a double allylboration reagent targeting 1,5-syn-(E)-diols: Application to the synthesis of the C(23)-C(40) fragment of tetrafibricin
Nuhant, Philippe,Kister, Jeremy,Lira, Ricardo,Sorg, Achim,Roush, William R.
experimental part, p. 6497 - 6512 (2011/10/01)
Interest in the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin prompted us to develop a new method for the synthesis of 1,5-syn-(E)-diols. Toward this end, the kinetically controlled hydroboration of allenes 6, 33, ent-39, 42, and 45 with the Soderquist borane 25R were studied. Tetrabutylammonium allenyltrifluoroborate 45 gave superior results and was utilized in a double allylboration sequence with two different aldehydes to provide the targeted 1,5-syn-(E)-diols in generally high yields (72-98%), and with high enantioselectivity (>95% ee), diastereoselectivity (dr >20:1), and (E)/(Z) selectivity (>20:1). This new method was applied to the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin.
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
