949886-66-2Relevant academic research and scientific papers
Catalytic Enantioselective Arylation and Heteroarylation of Ketones with Organotitanium Reagents Generated In Situ
Matsuda, Atsushi,Ushimaru, Tomoya,Kobayashi, Yusuke,Harada, Toshiro
supporting information, p. 8605 - 8609 (2017/06/30)
A practical and useful, catalytic enantioselective method has been developed for the synthesis of tertiary diaryl and aryl heteroaryl carbinols starting from commercially available aromatic ketones and aryl or heteroaryl bromides. In this method, organotitanium reagents are generated in situ from the bromides by lithiation with nBuLi followed by transmetallation of the resulting organolithiums with ClTi(OiPr)3. Treatment of the ketones with the titanium reagents in the presence of (R)-3-(3,5-bistrifluoromehthylphenyl)-1,1′-bi-2-naphthol (BTFP-BINOL) affords the corresponding tertiary alcohols in high enantioselectivities and yields. The reaction can also start with furan and 2-thienyllithium. The method is operationally simple and can be conducted on a 10-mmol scale without any difficulties.
Asymmetric Direct 1,2-Addition of Aryl Grignard Reagents to Aryl Alkyl Ketones
Osakama, Kazuki,Nakajima, Makoto
supporting information, p. 236 - 239 (2016/02/03)
The enantioselective addition of Grignard reagents to ketones was promoted by a BINOL derivative bearing alkyl chains at the 3,3′-positions. This is the first asymmetric direct aryl Grignard addition to ketones reported to date. A variety of tertiary diaryl alcohols could be obtained in high yields and enantioselectivities without using any other metal source.
MgBr2-promoted enantioselectIVe aryl addition of ArTi(OiPr)3 to ketones catalyzed by a titanium(IV) catalyst of N,N′-sulfonylated (1R,2R)-cyclohexane-1,2-diamine
Shu, Chao-Chi,Zhou, Shuangliu,Gau, Han-Mou
, p. 98391 - 98398 (2015/12/04)
MgBr2-promoted asymmetric addition of ArTi(OiPr)3 to ketones catalyzed by a titanium catalyst of N,N′-sulfonylated (1R,2R)-cyclohexane-1,2-diamines is reported, and results showed that the chiral N,N′-sulfonylated cyclohex
Full chirality transfer in the conversion of secondary alcohols into tertiary boronic esters and alcohols using lithiation-borylation reactions
Bagutski, Viktor,French, Rosalind M.,Aggarwal, Varinder K.
supporting information; experimental part, p. 5142 - 5145 (2010/10/20)
New conditions, full transfer: Using MgBr2/MeOH as an additive now provides essentially 100 % retention of configuration in the lithiation-borylation reaction, thus leading to tertiary boronic esters (or tertiary alcohols) with exceptionally hi
