Download PDF
Synfacts 2015; 11(7): 0719
DOI: 10.1055/s-0034-1380926
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Copper Hydride Catalyzed Synthesis of 2,3-Disubstituted Indolines

Contributor(s):
Hisashi Yamamoto
,
Biplab Maji
Ascic E, Buchwald SL * Massachusetts Institute of Technology, Cambridge, USA
Highly Diastereo- and Enantioselective CuH-Catalyzed Synthesis of 2,3-Disubstituted Indolines.

J. Am. Chem. Soc. 2015;
137: 4666-4669
CrossrefGoogle Scholar
Further Information

Publication History

Publication Date:
17 June 2015 (online)

 
 PDF Download Permissions and Reprints

Key words

indolines - Markovnikov addition - organometallic reagents - copper

Significance

The L*CuH-catalyzed diastereo- and enantioselective synthesis of 2,3-disubstituted cis-indolines proceeds under mild conditions and tolerates bulky functional groups, including heterocycles, olefins, or substituted aromatic rings. A methyl substituent at the C-4 position of the indoline ring results in lower reactivity.


#

Comment

The yield of the reaction is significantly dependent on the choice of alcohol. t-BuOD is superior to t-BuOH, as it reduced the amount of byproduct by slowing the protonolysis of B. Interestingly, the reaction is highly cis-diastereoselective. Addition of triphenylphosphine as a secondary ligand significantly improves the catalyst turnover.


#
#


   Permissions and Reprints