HMPA promotes retro-aldol reaction, resulting in syn-selective addition oflithiated 1-naphthylacetonitrile to aromatic aldehydes

Authors
Carlier, PR Lo, CWS Lo, MMC Wan, NC Williams, ID
Citation
Pr. Carlier et al., HMPA promotes retro-aldol reaction, resulting in syn-selective addition oflithiated 1-naphthylacetonitrile to aromatic aldehydes, ORG LETT, 2(16), 2000, pp. 2443-2445
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
16
Year of publication
2000
Pages
2443 - 2445
Database
ISI
SICI code
1523-7060(20000810)2:16<2443:HPRRRI>2.0.ZU;2-O
Abstract
[GRAPHICS] In HMPA-THF solution, lithiated 1-naphthylacetonitrile undergoes highly syn -selective addition to aromatic aldehydes, providing the first access to su ch syn-aldols. Syn-selectivity is also observed with two other arylacetonit riles, Aldolate equilibration and crossover experiments demonstrate that HM PA promotes retro aldol reaction and that aldol diastereoselectivity under these conditions is thermodynamically controlled.