The effect of ligands on the change of diastereoselectivity dimerization of 2-(naphthyl-1)cyclopropanedicarboxylate in the presence of GaCl3

The effect of ligands on the change of diastereoselectivity dimerization of 2-(naphthyl-1)cyclopropanedicarboxylate in the presence of GaCl3 Full article

Journal

Arkivoc
ISSN: 1551-7012 , E-ISSN: 1551-7004

Output data

Year: 2016, Number: 5, Pages: 362-375 Pages count : 14 DOI: 10.24820/ark.5550190.p009.860

Authors

Novikov Roman A. ^1,2 , Borisov Denis D. ¹ , Tomilov Yury V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
2	V. A. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 32 Vavilov st., 119991 Moscow, Russian Federation

A new method to regulate the diastereoselectivity of reactions of donor-acceptor cyclopropanes by ligand control has been found. The method has been demonstrated for [4+2]-cyclodimerization of 2-(1-naphthyl)cyclopropanedicarboxylate to give polysubstituted tetrahydrophenanthrenes in the presence of GaCl3 as an example. If tetrahydrofuran is used as the ligand, the trans,trans-isomer is formed exclusively, whereas if 1-formylpyrene is used, diastereoselectivity changes almost completely and the trans,cis-isomer is formed. A possible mechanism of diastereoselectivity change has been suggested and studied.

Novikov R.A. , Borisov D.D. , Tomilov Y.V.
The effect of ligands on the change of diastereoselectivity dimerization of 2-(naphthyl-1)cyclopropanedicarboxylate in the presence of GaCl3
Arkivoc. 2016. N5. P.362-375. DOI: 10.24820/ark.5550190.p009.860 Scopus OpenAlex

≡ Scopus:	2-s2.0-85046249419
≡ OpenAlex:	W2775590221