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BIFUNCTIONAL CHIRAL AUXILIARIES-8 - UTILIZATION OF TARTARIC ACID-DERIVED AUXILIARIES IN ALDOL AND ALKYLATION REACTIONS

Abstract:

The boron enolates of three new homochiral C2 symmetric 1,3-diacylimidazolidin-2-ones prepared from natural tartaric acid undergo highly diastereoselective aldol and alkylation reactions. Cleavage of these diastereomerically pure, adducts gives homochiral (1R,2S)-1-phenyl-2-methylpropane-1,3-diol and (2R,3R)-3-hydroxy-3-phenyl-2-methylpropanoic acid and (2S)-3-phenyl-2-methylpropan-1-ol (>92% ee). One of these auxiliaries, 4,5-dimethylimidazolidin-2-one, has the lowest effective molecular ...

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Publication status:
Published

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Journal:
TETRAHEDRON
Volume:
50
Issue:
25
Pages:
7521-7534
Publication date:
1994-06-20
DOI:
ISSN:
0040-4020
URN:
uuid:b7de1cc3-8052-47ee-b61c-d15c2bd771d6
Source identifiers:
110864
Local pid:
pubs:110864
Language:
English

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