219680-01-0Relevant academic research and scientific papers
Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols
Jiang, Yao,Schaus, Scott E.
supporting information, p. 1544 - 1548 (2017/02/05)
Chiral biphenols catalyze the asymmetric Petasis borono-Mannich allylation of aldehydes and amines through the use of a bench-stable allyldioxaborolane. The reaction proceeds via a two-step, one-pot process and requires 2–8 mole % of 3,3′-Ph2-BINOL as the optimal catalyst. Under microwave heating the reaction affords chiral homoallylic amines in excellent yields (up to 99 %) and high enantioselectivies (er up to 99:1). The catalytic reaction is a true multicomponent condensation reaction whereas both the aldehyde and the amine can possess a wide range of structural and electronic properties. Use of crotyldioxaborolane in the reaction results in stereodivergent products with anti- and syn-diastereomers both in good diastereoselectivities and enantioselectivities from the corresponding E- and Z-borolane stereoisomers.
Development of the first menthane-based chiral bis(π-allylpalladium) catalysis: Asymmetric allylation of imines
Fernandes, Rodney A.,Chaudhari, Dipali A.
experimental part, p. 1945 - 1952 (2012/05/20)
A new ethylidene menthane-based chiral π-allylpalladium complex catalyzes the asymmetric allylation of various imines with allyltributylstannane and 1 equiv. of water to give chiral homoallylamines in good yields and enantioselectivities. The reaction was carried out essentially under neutral conditions and displayed a good transfer of chiral information from the menthane skeleton through the formation of a bis(π-allylpalladium) species. This is the first example of menthane-based chiral bis(π-allylpalladium) catalysis. A menthane-based chiral π-allylpalladium-catalyzed asymmetric allylation of various imines has been developed giving chiral homoallylamines in good yields and enantioselectivities. The reaction displays a good transfer of chiral information from the menthane skeleton through the formation of a bis(π-allylpalladium) complex. Copyright
