Catalytic enantioselective amination of silyl enol ethers using chiral dirhodium(II) carboxylates: Asymmetric formal synthesis of (-)-metazocine

Masahiro Anada; Masahiko Tanaka; Takuya Washio; Minoru Yamawaki; Takumi Abe; Shunichi Hashimoto

doi:10.1021/ol702019b

Catalytic enantioselective amination of silyl enol ethers using chiral dirhodium(II) carboxylates: Asymmetric formal synthesis of (-)-metazocine

Masahiro Anada, Masahiko Tanaka, Takuya Washio, Minoru Yamawaki, Takumi Abe, Shunichi Hashimoto

Research output: Contribution to journal › Article › peer-review

94 Citations (Scopus)

Abstract

(Chemical Equation Presented) 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.

Original language	English
Pages (from-to)	4559-4562
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	22
DOIs	https://doi.org/10.1021/ol702019b
Publication status	Published - Oct 25 2007
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol702019b

Cite this

@article{18fcb07b13374c6a81011b32a27e4820,

title = "Catalytic enantioselective amination of silyl enol ethers using chiral dirhodium(II) carboxylates: Asymmetric formal synthesis of (-)-metazocine",

abstract = "(Chemical Equation Presented) 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.",

author = "Masahiro Anada and Masahiko Tanaka and Takuya Washio and Minoru Yamawaki and Takumi Abe and Shunichi Hashimoto",

year = "2007",

month = oct,

day = "25",

doi = "10.1021/ol702019b",

language = "English",

volume = "9",

pages = "4559--4562",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "22",

}

TY - JOUR

T1 - Catalytic enantioselective amination of silyl enol ethers using chiral dirhodium(II) carboxylates

T2 - Asymmetric formal synthesis of (-)-metazocine

AU - Anada, Masahiro

AU - Tanaka, Masahiko

AU - Washio, Takuya

AU - Yamawaki, Minoru

AU - Abe, Takumi

AU - Hashimoto, Shunichi

PY - 2007/10/25

Y1 - 2007/10/25

N2 - (Chemical Equation Presented) 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.

AB - (Chemical Equation Presented) 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.

UR - http://www.scopus.com/inward/record.url?scp=35948970147&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=35948970147&partnerID=8YFLogxK

U2 - 10.1021/ol702019b

DO - 10.1021/ol702019b

M3 - Article

C2 - 17894504

AN - SCOPUS:35948970147

SN - 1523-7060

VL - 9

SP - 4559

EP - 4562

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Catalytic enantioselective amination of silyl enol ethers using chiral dirhodium(II) carboxylates: Asymmetric formal synthesis of (-)-metazocine

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this