1100345-77-4Relevant academic research and scientific papers
Strict reagent control in the asymmetric allylboration of N-TIPS-α-amino aldehydes with the B-allyl-10-TMS-9-borabicyclo[3.3.2] decanes
Soto-Cairoli, Buddy,Soderquist, John A.
, p. 401 - 404 (2009)
(Chemical Equation Presented) The allylboration of enantiomerically pure N-triisopropylsilyl-α-amino aldehydes (2) with B-allyl-10-trimethylsilyl- 9-borabicyclo[3.3.2]decanes (1) proceeds cleanly at -78 °C, exhibiting essentially complete reagent control. After an oxidative workup, an HOAc-mediated N→O TIPS rearrangement facilitates the clean formation of stable O-TIPS protected β-amino alcohol derivatives 3 which are isolated in 60-83% yields in >96% de and >99% ee. For the leucinal series (R = i-Bu), an efficient entry to either statine (8aSS) or epi-statine (8aRS) is reported illustrating the versatility of this potent 1/2 combination.
