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Recent progress in a chiral multinucleating system utilizing tartaric acid esters
Author(s) -
Ukaji Yutaka,
Inomata Katsuhiko
Publication year - 2010
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.201000002
Subject(s) - tartaric acid , chiral auxiliary , chemistry , reagent , enantioselective synthesis , nucleophile , combinatorial chemistry , organic chemistry , cycloaddition , hydroxylamine , catalysis , citric acid
In order to develop a practical method for the construction of chiral molecules, we have designed a novel chiral reaction system possessing multi‐metal centers utilizing tartaric acid ester as a chiral auxiliary. Based on this concept, we have developed an asymmetric 1,3‐dipolar cycloaddition reaction of azomethine imines, an asymmetric hetero Diels‐Alder reaction of nitroso compounds, an asymmetric Diels‐Alder reaction of o ‐quinodimethanes. Furthermore, an asymmetric nucleophilic addition of alkynylzinc reagents, prepared in situ from dialkylzinc and 1‐alkynes, to nitrones was achieved with high level of stereocontrol. In the last case, the addition of methylzinc salt of a product‐like racemic hydroxylamine was found to be effective for unprecedented enhancement of enantioselectivity. © 2010 The Japan Chemical Journal Forum and Wiley Periodicals, Inc. Chem Rec 10: 173–187; 2010: Published online in Wiley InterScience ( www.interscience.wiley.com ) DOI 10.1002/tcr.2012