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Stereoselective Intramolecular Nitrone Cycloaddition in the Synthesis of Lasubine II
Author(s) -
Hoffmann Reinhard W.,
Endesfelder Andreas
Publication year - 1986
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198619861102
Subject(s) - intramolecular force , cycloaddition , chemistry , nitrone , stereoselectivity , selectivity , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
The intramolecular cycloaddition of α‐substituted N ‐alkenylnitrones 2 leads to the 7‐oxa‐1‐azanorbornanes 6, 7 , and 8 with a selectivity of ca. 80% in favor of the exo , exo ‐disubstituted compound 6 . The latter can be reduced to give the all ‐ cis ‐2,6‐disubstituted 4‐hydroxypiperidines 4 which are key compounds for the synthesis of certain alkaloids as demonstrated by the synthesis of lasubine II.