First Synthesis of Medium-Sized Ring Allenyl Lactams

6533b821fe1ef96bd127c120

RESEARCH PRODUCT

First Synthesis of Medium-Sized Ring Allenyl Lactams

Dieter Schollmeyer Moritz Perscheid Udo Nubbemeyer

subject

Claisen rearrangement chemistry.chemical_compound Olefin fiber chemistry Stereochemistry Allene Organic Chemistry Physical and Theoretical Chemistry Ring (chemistry)

description

Medium-sized lactams bearing an axially chiral allene unit have been synthesized by using an aza-ketene Claisen rearrangement. Starting from 2-alkynylpiperidines or 2-alkynylazepines, ring enlargement enabled the highly diastereoselective formation of 10- or 11-membered lactams with a 4,5-allene subunit. X-ray analysis of the allenylacezinone showed the presence of a strained cumulated olefin system with a defined arrangement of the functional groups. The cyclic allenes were found to be stable upon heating up to 50 °C.

year	journal	country	edition	language
2011-08-17	European Journal of Organic Chemistry

https://doi.org/10.1002/ejoc.201100830

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