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Mechanisms of nucleophilic substitutions of acetals

Abstract:
The nucleophilic substitution of (+)-(R)-benzaldehyde methyl isopropyl acetal (αR)-1 (93% ee) and (+)-(R)-o-anisaldehyde methyl isopropyl acetal (αR)-2 (homochiral) with Me2CuLi-BF3·OEt2 occurs completely chemoselectively to afford (+)-(αR)-α-methyl(benzyl) isopropyl ether (+)-(αR)-3 (40% ee) and (+)-(αR)-α-methyl(o-methoxybenzyl) isopropyl ether (+)-(αR)-4 (34% ee) respectively, demonstrating that the mechanism of the former reaction involves a free oxonium ion to the extent of 56% and the latter to the extent of 66%.
Publication status:
Published

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Publisher copy:
10.1039/a804230f

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 More from this journal
Issue:
15
Pages:
2231-2233
Publication date:
1998-08-07
DOI:
EISSN:
1364-5463
ISSN:
0300-922X
Language:
English
Pubs id:
pubs:110626
UUID:
uuid:cd498754-fcc8-482b-99f8-f4056267dc04
Local pid:
pubs:110626
Source identifiers:
110626
Deposit date:
2012-12-19

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