133398-25-1Relevant articles and documents
Copper-Catalyzed γ-Selective and Stereospecific Allylic Cross-Coupling with Secondary Alkylboranes
Yasuda, Yuto,Nagao, Kazunori,Shido, Yoshinori,Mori, Seiji,Ohmiya, Hirohisa,Sawamura, Masaya
supporting information, p. 9666 - 9670 (2015/06/30)
The scope of the copper-catalyzed coupling reactions between organoboron compounds and allylic phosphates is expanded significantly by employing triphenylphosphine as a ligand for copper, allowing the use of secondary alkylboron compounds. The reaction proceeds with complete γ-E-selectivity and preferential 1,3-syn stereoselectivity. The reaction of γ-silicon-substituted allylic phosphates affords enantioenriched α-stereogenic allylsilanes.
Stereoselective synthesis of (Z)- and (E)-allylic silanes by copper- mediated substitution reactions of allylic carbamates with grignard reagents
Smitrovich, Jacqueline H.,Woerpel
, p. 1601 - 1614 (2007/10/03)
Both (Z)- and (E)-allylic silanes were prepared with high stereoselectivity by the copper-mediated substitution of allylic carbamates by organometallic reagents. The reaction of alkylmagnesium reagents with (E)- allylic carbamates provides (Z)-allylic silanes, whereas both alkylmagnesium and alkyllithium reagents react with (Z)-allylic carbamates to afford (E)- allylic silanes. Because Grignard reagents are often more facile to prepare than alkyllithium species, these reagents are the optimal nucleophiles for the synthesis of both (Z)- and (E)-allylic silanes. This method also allows readily available nonracemic allylic carbamates to be converted to chiral, nonracemic (Z)- and (E)-allylic silanes with high stereoselectivity.
Synthesis of chiral (E)-crotylsilanes: [3R- and 3S-]-(4E)-methyl 3-(dimethylphenylsilyl)-4-hexenoate [ 4-Hexenoic acid, 3-(dimethylphenylsilyl)-, methyl ester, [(R)-, and (S)-(E)-]- ]
Beresis, Richard T.,Solomon, Jason S.,Yang, Michael G.,Jain, Nareshkumar F.,Panek, James S.,Madan, Pradeep,Wolff, Steven
, p. 78 - 78 (2017/10/03)
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