Chemoenzymatic Synthesis of Chiral 1‐Benzyl‐5‐(hydroxymethyl)‐2‐piperidone Enabled by Lipase AK‐Mediated Desymmetrization of Prochiral 1,3‐Diol and Its Diacetate | Zendy

Khong Duc Thinh | Zendy; Pamarthy Varsha Siri | Zendy; Gallagher Timothy | Zendy; Judeh Zaher M. A. | Zendy

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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.

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