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Updated: Jul 5, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Base-induced sequential cyclization-rearrangement of enantioenriched 3-aminoalkanoates to five- and seven-membered
Takeo Sakai1, Ken-Ichi Yamada, Kiyoshi Tomioka
1Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Japan.
Abstract:
By treatment with tBuLi, linear 3-aminoalkanoates (4) were converted stereoselectively into five- and seven-membered lactams (trans-5 and cis-6). Initial cyclization to azetidin-2-one with subsequent aza-[1,2] and [2,3] rearrangement is the probable mechanistic pathway from 4 to 5 and 6. Although enantioenriched 4 was converted into nearly racemic 5 and 6, a linear 3-amino-2-methylalkanoate (17) with 90 % ee bearing chirality at the ester alpha-position afforded an all-cis seven-membered lactam (18) bearing three asymmetric centers with 85 % ee.
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