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Stereoelectronic effects in the DIBAL reduction of aryl-1,2-ethanediol benzylidene acetals

✍ Scribed by Donald R Gauthier Jr.; Ronald H Szumigala Jr.; Joseph D Armstrong III; R.P Volante

Book ID: 104231518
Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 79 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)01466-6

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✦ Synopsis

Reduction of benzylidene acetal 8 with DIBAL-H selectively gave 4 in 89% yield. 1-Aryl-1,2-diol benzylidene acetals display unusual regioselectivity with electron withdrawing groups on the aryl group.

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