Diastereoselective alkylations of chiral, phosphorus-stabilized carbanions:: N-alkyl substituent effects in P-alkyl-1,3,2-diazaphosphorinane 2-oxides

A systematic study of the diastereoselective alkylation of anions derived from racemic N-substituted P-alkyl 1,3,2-diazaphosphorinane 2-oxides was carried out with variation of the N-substituent. High diastereoselectivity for the methylation of a P-benzyl anion has been achieved with N-neopentyl derivative 5d. Similarly, a P-ethyl anion derived from N-neopentyl derivative 6d showed high diastereoselectivity upon benzylation. The observed difference in alkylation diastereoselectivity between P-ethyl and P-benzyl anions for various N-alkyl substituents is discussed.