Catalytic Enantioselective Amination of Silyl Enol Ethers Using Chiral Dirhodium(II) Carboxylates:  Asymmetric Formal Synthesis of (−)-Metazocine

Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate], Rh2(S-TFPTTL)4, is an exceptionally efficient catalyst for enantioselective aminations of silyl enol ethers derived from acyclic ketones or α,β-enones with [N-(2-nitrophenylsulfonyl)imino]phenyliodinane (NsNIPh), providing N-(2-nitr...

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Published inOrganic letters Vol. 9; no. 22; pp. 4559 - 4562
Main Authors Anada, Masahiro, Tanaka, Masahiko, Washio, Takuya, Yamawaki, Minoru, Abe, Takumi, Hashimoto, Shunichi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 25.10.2007
Amer Chemical Soc
Subjects
Amination
Catalysis
Chemistry
Chemistry, Organic
Ethers - chemistry
Molecular Structure
Morphinans - chemical synthesis
Organometallic Compounds - chemistry
Physical Sciences
Rhodium - chemistry
Science & Technology
KETONES
ELECTROPHILIC ALPHA-AMINATION
RH(II) CATALYST
COMPLEXES
HYDROSILYLATION
AMIDATION
RHODIUM(II)-CATALYZED AZIRIDINATION
BENZOMORPHANS
EFFICIENT
INSERTIONS
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Summary:Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate], Rh2(S-TFPTTL)4, is an exceptionally efficient catalyst for enantioselective aminations of silyl enol ethers derived from acyclic ketones or α,β-enones with [N-(2-nitrophenylsulfonyl)imino]phenyliodinane (NsNIPh), providing N-(2-nitrophenylsulfonyl)-α-amino ketones in high yields and with enantioselectivities of up to 95% ee. The effectiveness of the present catalytic protocol has been demonstrated by an asymmetric formal synthesis of (−)-metazocine.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol702019b