222178-77-0Relevant academic research and scientific papers
A new lithium alkoxide accelerated diastereoselective cyanation of ketones
Wilkinson, H. Scott,Grover, Paul T.,Vandenbossche, Charles P.,Bakale, Roger P.,Bhongle, Nandkumar N.,Wald, Stephen A.,Senanayake, Chris H.
, p. 553 - 556 (2007/10/03)
(Matrix presented) A remarkably general lithium heteroatom assisted TMSCN or TBSCN addition to aldehydes and ketones has been discovered. The process provides excellent selectivities and high rates. Conformationally constrained ketones such as camphor, fenchone, and nopinone give excellent diastereoselectivities with TMSCN. Reduction of 2 provided diastereopure amino alcohol 3 in good yield. α- and β-Methyl cyclohexanones with TBSCN-LiOR afford high diastereoselectivities and yields.
Asymmetric electrophilic methoxyselenenylations and cyclizations with 3- camphorseleno derivatives
Back, Thomas G.,Dyck, Brian P.,Nan, Siqiao
, p. 3191 - 3208 (2007/10/03)
A series of novel 3-camphor-based diselenides, differing in substitution at C-2, was prepared. The corresponding allyl selenides were used as protecting groups for the diselenide moieties in several subsequent transformations. The diastereoselective methoxyselenenylation of alkenes was achieved with methanolic selenenyl triflates derived from the camphor diselenides, of which the 2-keto analogue proved the most effective. Diastereoselective electrophilic cyclizations of unsaturated alcohols, carboxylic acids and amides were most effectively performed with the corresponding selenenyl chloride, containing a spiro-oxazolidinone moiety at C-2 of the camphor residue. The absolute configurations of several products were determined by reductive deselenization.
