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Lithiated N ‐pivaloyl‐tetrahydroisoquinoline—a Supernuclephile
Author(s) -
Lohmann JeanJacques,
Seebach Dieter,
Syfrig Max A.,
Yoshifuji Masaaki
Publication year - 1981
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198101281
Subject(s) - alkyl , deprotonation , alkylation , derivative (finance) , medicinal chemistry , nucleophile , chemistry , primary (astronomy) , lithium (medication) , organic chemistry , ion , biology , business , catalysis , physics , finance , astronomy , endocrinology
The high nucleophilicity of the lithium derivative of (1) , X = CO t Bu , permits alkylation at C‐1 using primary alkyl chlorides, secondary alkyl iodides or easily deprotonated ketones. The pivaloyl group in the product (2) can be reductively removed. 1,1‐Disubstituted tetra‐hydroisoquinolines such as (3) can be obtained in this way.