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Chemoenzymatic Synthesis of Chiral 1‐Benzyl‐5‐(hydroxymethyl)‐2‐piperidone Enabled by Lipase AK‐Mediated Desymmetrization of Prochiral 1,3‐Diol and Its Diacetate
Author(s) -
Khong Duc Thinh,
Pamarthy Varsha Siri,
Gallagher Timothy,
Judeh Zaher M. A.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600262
Subject(s) - desymmetrization , chemistry , hydroxymethyl , synthon , yield (engineering) , lipase , diol , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , enzyme , materials science , metallurgy
The synthesis of ( R )‐1‐benzyl‐5‐(hydroxymethyl)‐2‐piperidone ( 1 ) from key synthon monoacetate ( R )‐ 3 has been accomplished conveniently in 6 steps with 93 % ee and in 44 % overall yield. The key step involved lipase AK‐mediated desymmetrization of diol 4 to produce monoacetate ( R )‐ 3 in 93 % ee and 93 % yield. Additionally, lipase AK‐mediated desymmetrization of diacetate 5 readily provided access to monoacetate ( S )‐ 3 in 93 % ee and 54 % yield.