Synthesis p. 941 - 948 (1996)
Update date:2022-08-05
Topics:
Enders, Dieter
Gr?bner, Robert
Raabe, Gerhard
Runsink, Jan
2-Alkyl-substituted lactams 4 were synthesized in good overall yields and high enantiomeric purities (ee = 71-99%) by α-alkylation of chiral N-(dialkylamino)lactams 2 and subsequent reductive N-N bond cleavage of the resulting lactams 3 with lithium in liquid ammonia. The lactams 2, in turn, were prepared in good yields by cyclization of ω-chloroalkanohydrazides 1 with sodium hydride. Acidic hydrolysis of lactams 4 leads to γ-aminobutanoic acid (GABA) derivatives 5 (ee ≤ 99%). The absolute configuration was determined by polarimetry and an X-ray structure analysis of (S,S)-3e'.
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Doi:10.1021/ic951386v
(1996)Doi:10.1039/P19960001809
(1996)Doi:10.1016/0040-4039(96)01352-4
(1996)Doi:10.1021/ja970709e
(1997)Doi:10.1016/0040-4039(96)01517-1
(1996)Doi:10.1016/0022-328X(96)06200-6
(1996)