286366-50-5Relevant academic research and scientific papers
Atroposelective attack of nucleophiles on 2-formyl-1-naphthamides and their derivatives: Chelation and non-chelation control
Clayden, Jonathan,McCarthy, Catherine,Westlund, Neil,Frampton, Christopher S.
, p. 1363 - 1378 (2000)
Organometallic nucleophiles attack 2-formyl-1-naphthamides to give secondary alcohols with widely varying atroposelectivity. By careful choice of reagent, selectivities of up to >99:1 in favour of either the anti or the syn atropisomer can be obtained. Ethers and amines may be synthesised atroposelectively from acetals or imines. The sense of the selectivity is determined by the reactive conformation of the Ar-CHO bond, itself dependent on the coordinating and chelating ability of the nucleophile's counterion. The roles of conformation, Lewis acids, and chelation/non-chelation control in relation to stereoselectivity are discussed.
Atroposelective attack of nucleophiles and electrophiles on 2-acyI-l-naphthamides and their enolates
Clayden, Jonathan,Westlund, Neil,Beddocs, Roy L.,Helliwell, Madeleine
, p. 1351 - 1361 (2007/10/03)
Organolithiums, Grignard reagents and borohydride reducing agents attack 2-acyl-l-naphthamides to give tertiary and secondary alcohols with high or complete atroposelectivity. High levels of stereoselectivity can also be obtained in the alkylations of eno
