Hydrogen-Borrowing Alkylation of 1,2-Amino Alcohols in the Synthesis of Enantioenriched γ-Aminobutyric Acids.

To probe the effect of sterics on the reaction, we examined smaller and larger nitrogen protecting groups for both alaninols 4 a – c and d 2 ‐glycinols 5 a – c (Table 2 ). In both cases, we saw a clear trend between increasing steric bulk of the nitrogen protecting group and a decreasing degree of intermediate deprotonation—indicated either by racemization in products 6 a – c , or by loss of deuterium incorporation in d 2 ‐glycine derivatives 7 a – c .

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