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Capture-ROMP-release: application to the synthesis of amines and alkyl hydrazines

✍ Scribed by Shubhasish Mukherjee; Kevin W.C Poon; Daniel L Flynn; Paul R Hanson

Book ID
104254371
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
157 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

Application of a capture-ROMP-release strategy for the chromatography-free purification of Mitsunobu reaction products is described. Norbornenyl-tagged reagents are utilized for standard solution phase Mitsunobu chemistry. Post-reaction phase-switching is accomplished via in situ ring-opening metathesis polymerization (ROMP) followed by precipitation of the polymer with methanol. Release of the product from the polymer affords amines and alkyl hydrazine derivatives with good yields and purities.

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## Abstract Acyclic amines **1** were obtained by a nucleophilic aromatic substitution (S~N~Ar) reaction and __N__‐methylation followed by silane reduction. The optical resolution of C(aryl)–N(amine) bond atropisomers of amines **1** is described. We found that chiral acyclic amine **1a** can be re