Abstract
A new two-step, one-pot procedure is reported for the enantioselective synthesis of C2-symmetric diols derived from 1,2-phthalicdicarboxaldehyde. The first step involves the enantioselective addition of a dialkylzinc compound to one of the aldehyde groups, affording a lactol organozinc derivative. In the second step this lactol derivative is converted to the appropriate diol with the aid of a Grignard reagent and subsequent hydrolysis. This methodology also allows the synthesis of unsymmetric diols. © 2001 Elsevier Science Ltd.
| Original language | English |
|---|---|
| Pages (from-to) | 3933-3937 |
| Number of pages | 5 |
| Journal | Tetrahedron Letters |
| Volume | 42 |
| Issue number | 23 |
| DOIs | |
| Publication status | Published - 4 Jun 2001 |
Keywords
- 1,2 phthalicarboxaldehyde
- aldehyde derivative
- Grignard reagent
- lactone derivative
- reagent
- unclassified drug
- alkylation
- article
- chemical reaction
- diastereoisomer
- enantiomer
- hydrolysis
- stereochemistry
- synthesis