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Synlett 1996; 1996(7): 645-646
DOI: 10.1055/s-1996-5581
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Enantioselective Synthesis of 2-Alkyl-2-methyl-3-butenenitriles

Takashi Mino, Katsuyoshi Takagi, Masakazu Yamashita*
  • *Department of Molecular Science and Technology, Faculty of Engineering, Doshisha University, Tanabe, Kyoto 610-03, Japan, Fax: 81-774-65-6840, E-mail: myamashi@mail.doshisha.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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2-Alkyl-2-methyl-3-butenenitriles which have an asymmetric quaternary carbon atom at the a-position were obtained from 2-methyl-2-butenal SAMP hydrazone in good enantiomeric excesses (e.e. = 73-95 %). This shows that diastereoselective alkylation occurred at the a-position and the a,b-unsaturated double bond migrated to b,g. The absolute configuration of 2-benzyl-2-methyl-3-butenenitrile was determined as R by derivatization and comparison of optical rotation.

diastereoselective alkylation - chiral nitrile - quaternary carbon atom - SAMP hydrazone

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