TY  - JOUR
A1  - Krüger, Tobias
A1  - Linker, Torsten
T1  - Synthesis of gamma-spirolactams by Birch reduction of arenes
T2  - European journal of organic chemistry
N2  - A convenient method for the synthesis of gamma-spirolactams in only three steps is described. Birch reduction of inexpensive and commercially available aromatic carboxylic acids in the presence of chloroacetonitrile affords nitriles in moderate to good yields. Suitable precursors are methyl-substituted benzoic acids, naphthoic, and anthroic acid. Subsequent catalytic hydrogenation proceeds smoothly with PtO2 or Raney Ni as catalysts and lactams are isolated in excellent yields and stereoselectivities. Thus, up to 3 new stereogenic centers can be constructed as sole diastereomers from achiral benzoic acids. Furthermore, it is possible to control the degree of saturation at different pressures, affording products with 0, 1, or 2 double bonds. Overall, more than 15 new gamma-spirolactams have been synthesized in analytically pure form.
KW  - Arenes
KW  - Birch reduction
KW  - Hydrogenation
KW  - Lactams
KW  - Synthetic methods
Y1  - 2021
UR  - https://publishup.uni-potsdam.de/frontdoor/index/index/docId/57630
SN  - 1099-0690
VL  - 2021
IS  - 10
SP  - 1585
EP  - 1591
PB  - Wiley-VCH
CY  - Weinheim
ER  -