Enantioselective Palladium‐Catalyzed N‐Allylation of Lactams | Zendy

Visse Robin | Zendy; Fidan Mesut | Zendy; Götzinger Alissa | Zendy; Motzny Angelika | Zendy; Jeddi Samir | Zendy; Braun Manfred | Zendy

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Enantioselective Palladium‐Catalyzed N‐Allylation of Lactams

Author(s) -

Visse Robin,

Fidan Mesut,

Götzinger Alissa,

Motzny Angelika,

Jeddi Samir,

Braun Manfred

Publication year - 2018

Publication title -

chemistryselect

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.437

H-Index - 34

ISSN - 2365-6549

DOI - 10.1002/slct.201801233

Subject(s) - enantioselective synthesis , palladium , catalysis , deprotonation , chemistry , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , ion

N‐Deprotonated five‐, six‐, seven, and nine‐membered lactams undergo smooth palladium‐catalyzed N‐allylation with methyl‐(pent‐3‐en‐2‐yl)‐carbonate or 2‐chloro‐3‐pentene. With axially chiral bisphosphane ligands, enantioselectivities ranging from 83 to 97% ee are reached. The configuration of one of the allylation products is assigned unambiguously by the preparation of a relay compound and by analogy to the others. Using the enantioselective allylation protocol as a key step, δ‐valerolactam is converted into (4 S ,9a R )‐4‐methylquinolizidine.

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