Highly enantioselective michael additions of indole to benzylidene malonate using simple bis(oxazoline) ligands: importance of metal/ligand ratio.Org Lett. 2006 Dec 21; 8(26):6099-102.OL
Abstract
[Structure: see text] Simple bis(oxazoline) ligands, especially azabis(oxazolines), can catalyze the copper-catalyzed addition of indoles to benzylidene malonates in up to >99% ee, provided that excess of chiral ligand is avoided. The paradigm followed in many asymmetric catalyses that an excess of chiral ligand with respect to the metal should improve enantioselectivity because a background reaction by free metal is suppressed, is not applicable here, which might call for revisiting some of the many copper(II)-bis(oxazoline)-catalyzed processes known.
Pub Type(s)
Journal Article
Research Support, Non-U.S. Gov't
Language
eng
PubMed ID
17165939
Citation
Rasappan, Ramesh, et al. "Highly Enantioselective Michael Additions of Indole to Benzylidene Malonate Using Simple Bis(oxazoline) Ligands: Importance of Metal/ligand Ratio." Organic Letters, vol. 8, no. 26, 2006, pp. 6099-102.
Rasappan R, Hager M, Gissibl A, et al. Highly enantioselective michael additions of indole to benzylidene malonate using simple bis(oxazoline) ligands: importance of metal/ligand ratio. Org Lett. 2006;8(26):6099-102.
Rasappan, R., Hager, M., Gissibl, A., & Reiser, O. (2006). Highly enantioselective michael additions of indole to benzylidene malonate using simple bis(oxazoline) ligands: importance of metal/ligand ratio. Organic Letters, 8(26), 6099-102.
Rasappan R, et al. Highly Enantioselective Michael Additions of Indole to Benzylidene Malonate Using Simple Bis(oxazoline) Ligands: Importance of Metal/ligand Ratio. Org Lett. 2006 Dec 21;8(26):6099-102. PubMed PMID: 17165939.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Highly enantioselective michael additions of indole to benzylidene malonate using simple bis(oxazoline) ligands: importance of metal/ligand ratio.
AU - Rasappan,Ramesh,
AU - Hager,Markus,
AU - Gissibl,Anja,
AU - Reiser,Oliver,
PY - 2006/12/15/pubmed
PY - 2007/9/26/medline
PY - 2006/12/15/entrez
SP - 6099
EP - 102
JF - Organic letters
JO - Org Lett
VL - 8
IS - 26
N2 - [Structure: see text] Simple bis(oxazoline) ligands, especially azabis(oxazolines), can catalyze the copper-catalyzed addition of indoles to benzylidene malonates in up to >99% ee, provided that excess of chiral ligand is avoided. The paradigm followed in many asymmetric catalyses that an excess of chiral ligand with respect to the metal should improve enantioselectivity because a background reaction by free metal is suppressed, is not applicable here, which might call for revisiting some of the many copper(II)-bis(oxazoline)-catalyzed processes known.
SN - 1523-7060
UR - https://www.unboundmedicine.com/medline/citation/17165939/Highly_enantioselective_michael_additions_of_indole_to_benzylidene_malonate_using_simple_bis_oxazoline__ligands:_importance_of_metal/ligand_ratio_
L2 - https://doi.org/10.1021/ol062697k
DB - PRIME
DP - Unbound Medicine
ER -
