BRUNNER, H and SCHIESSLING, H (1994) ENANTIOSELECTIVE CATALYSIS .89. ACYCLIC AND MACROCYCLIC BINAPHTHYL DERIVATIVES. BULLETIN DES SOCIETES CHIMIQUES BELGES, 103 (3). pp. 119-126. ISSN 0037-9646,
Full text not available from this repository.Abstract
A new synthesis of 3'-diformyl-2,2'-dihydroxy-1,1'-binaphthyl 1 is described. The macrocyclic compound 3 is formed by schiff base condensation of two moles of 1 with two moles of (FR)-1,2-Diamino-1,2-diphenylethane RR-2. Reduction of 3 yields the macrocycle 7. The binaphthylketones S-13 - S-15 are synthesised starting from (S)-3,3'-dicarboxy-2,2'-dihydroxy-1,1'-binaphthyl S-16 which is reacted with the corresponding Li-organic compound. By Schiff base condensation of S-13 - S-15 with (R)- and (S)-1-amino-1-phenylethane the new imines 16 - 21 are prepared. The compounds 3 and 16 - 20 are used as optically active ligands in the copper(II)-catalysed enantioselective cyclopropanation of styrene with ethyl diazoacetate. The product ethyl cis/trans-2-phenylcyclopropanecarboxylate is obtained with an optical induction up to 36.6%.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | HOST-GUEST COMPLEXATION; ASYMMETRIC DIHYDROXYLATION; |
| Depositing User: | Dr. Gernot Deinzer |
| Last Modified: | 19 Oct 2022 08:40 |
| URI: | https://pred.uni-regensburg.de/id/eprint/53426 |
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