1443008-03-4Relevant articles and documents
Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides
Marcyk, Paul T.,Jefferies, Latisha R.,AbuSalim, Deyaa I.,Pink, Maren,Baik, Mu-Hyun,Cook, Silas P.
, p. 1727 - 1731 (2019/01/21)
The direct, catalytic substitution of unactivated alcohols remains an undeveloped area of organic synthesis. Moreover, catalytic activation of this difficult electrophile with predictable stereo-outcomes presents an even more formidable challenge. Described herein is a simple iron-based catalyst system which provides the mild, direct conversion of secondary and tertiary alcohols to sulfonamides. Starting from enantioenriched alcohols, the intramolecular variant proceeds with stereoinversion to produce enantioenriched 2- and 2,2-subsituted pyrrolidines and indolines, without prior derivatization of the alcohol or solvolytic conditions.
Synthesis of quaternary α-methyl α-amino acids by asymmetric alkylation of pseudoephenamine alaninamide pivaldimine
Hugelshofer, Cedric L.,Mellem, Kevin T.,Myers, Andrew G.
, p. 3134 - 3137 (2013/07/26)
The utility of pseudoephenamine as a chiral auxiliary for the alkylative construction of quaternary α-methyl α-amino acids is demonstrated. The method is notable for the high diastereoselectivities of the alkylation reactions, for its versatility with respect to electrophilic substrate partners, and for its mild hydrolysis conditions, which provide α-amino acids without salt contaminants. Alternatively, α-amino esters can be obtained by direct alcoholysis.