Premium
A New Short Access to Amino Acids Incorporating an Aminocyclopropyl Moiety from N , N ‐Dibenzylcarboxamides
Author(s) -
Kordes Markus,
Winsel Harald,
de Meijere Armin
Publication year - 2000
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 - 10.1002/1099-0690(200009)2000:18<3235::aid-ejoc3235>3.0.co;2-7
Subject(s) - chemistry , cyclopropane , yield (engineering) , stereochemistry , medicinal chemistry , organic chemistry , ring (chemistry) , materials science , metallurgy
Our recently reported titanium‐mediated transformation of N , N ‐dialkylcarboxamides to cyclopropylamines has been applied to N , N ‐dibenzyl‐2‐benzyloxyacetamide using a variety of alkylmagnesium bromides to yield 1‐(benzyloxymethyl)‐1‐(dibenzylamino)cyclopropane ( 15a , 48%) and 2‐substituted analogs 15b−f (33−48%). These have been transformed in just a few steps into N ‐Boc‐protected methyl esters of 1‐aminocyclopropanecarboxylic acid ( 1 , 29% overall), coronamic acid ( 2 , 35%) and norcoronamic acid (21%), 2,3‐methanoglutamic acid ( 21g , 19%) and 2,3‐methanoornithine ( 21l , 12%). Similarly, the corresponding derivatives of 3,4‐methano‐γ‐aminobutyric acid ( 26 , 23%) and 4‐spirocyclopropane‐γ‐butyrolactam ( 32 , 44%) have been synthesized.