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Enantioselective Synthesis of (7 R ,8 R ,8a R )‐ and (7 S ,8 S ,8a S )‐7‐Hydroxy‐8‐indolizidinemethanol by 1,3‐Dipolar Cycloaddition of 1‐Pyrroline N ‐Oxide to Chiral Pentenoates
Author(s) -
Cordero Franca Maria,
Faggi Cristina,
De Sarlo Francesco,
Brandi Alberto
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(200011)2000:21<3595::aid-ejoc3595>3.0.co;2-n
Subject(s) - chemistry , enantioselective synthesis , 1,3 dipolar cycloaddition , cycloaddition , enantiomer , pyrroline , stereochemistry , oxide , organic chemistry , catalysis
The 1,3‐dipolar cycloadditions of pyrroline N ‐oxide ( 1 ) with (1 R ,2 S )‐ trans ‐2‐phenylcyclohexyl‐ and with (1 R ,2 S ,5 R )‐8‐phenylmenthyl‐pent‐2‐enoates ( 9 and 10 ) proceed with opposite diastereoselectivities. The two enantiomers of a new dihydroxyindolizidine, (+)‐ 6 and (−)‐ 6 , were synthesized using 4 and 5 , respectively, as the chiral auxiliary.