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Highly Enantioselective Asymmetric Autocatalysis of Pyrimidin‐5‐yl Alkanol Induced by Chiral 1,3‐Disubstituted Hydrocarbon Allenes
Author(s) -
Sato Itaru,
Matsueda Yohei,
Kadowaki Kousuke,
Yonekubo Shigeru,
Shibata Takanori,
Soai Kenso
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200210)85:10<3383::aid-hlca3383>3.0.co;2-b
Subject(s) - chemistry , autocatalysis , allene , enantioselective synthesis , heteroatom , pyrimidine , stereochemistry , chiral auxiliary , organic chemistry , catalysis , ring (chemistry)
1,3‐Disubstituted chiral allenes without any heteroatoms act as chiral initiators in the addition of (i‐Pr) 2 Zn to pyrimidine‐5‐carbaldehyde to afford, in combination with the subsequent asymmetric autocatalysis, chiral pyrimidin‐5‐yl alkanols with up to 98% ee. The absolute configuration of the pyrimidin‐5‐yl alkanol formed depend on that of the chiral allene.