115118-03-1Relevant articles and documents
Highly Diastereoselective Deprotonation and Substitution of Chiral 5,6-Dihydro-4H-1,2-oxazines
Hippeli, Claudia,Reissig, Hans-Ulrich
, p. 3884 - 3886 (1988)
Deprotonation of the chiral 1,2-oxazine 1 by n-butyllithium provides a carbanion which reacts highly diastereoselectively with electrophiles affording the substituted 1,2-oxazines 2.The overall substitution occurs under retention of configuration in most cases investigated.These remarkable results are in accord with recent ab initio calculations.
Lithiated 5,6-Dihydro-4H-1,2-oxazines: Synthesis, Highly Diastereoselective Reactions with Electrophiles, and Subsequent Transformations
Reissig, Hans-Ulrich,Hippeli, Claudia
, p. 115 - 127 (2007/10/02)
The 6-(trimethylsilyl)methyl-substituted 1,2-oxazine 1 can smoothly be deprotonated with n-butyllithium at C-4 to give a lithiated species which reacts with a variety of electrophiles to provide the new 1,2-oxazines 5-16 in good yields.Besides the prepara