Catalytic asymmetric conjugate addition of α-cyanoketones for the construction of a quaternary stereogenic center

Yuji Kawato; Noriko Takahashi; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1021/ol100183s

Catalytic asymmetric conjugate addition of α-cyanoketones for the construction of a quaternary stereogenic center

Yuji Kawato, Noriko Takahashi, Naoya Kumagai, Masakatsu Shibasaki

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

39 Citations (Scopus)

Abstract

(Figure Presented) The catalytic asymmetric conjugate addition of a-cyanoketone pronucleophiles to vinyl ketones promoted by a Y/1 catalyst is described. High enantioselectivity was observed for a range of aromatic vinyl ketones, providing 1,5-dicarbonyl compounds bearing an all-carbon quaternary stereogenic center. The product was successfully converted to a spiro-piperidine entity and a bicyclo[3.3.0]octane framework through either the reduction of nitrile or intramolecular pinacol coupling.

Original language	English
Pages (from-to)	1484-1487
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	7
DOIs	https://doi.org/10.1021/ol100183s
Publication status	Published - 2010 Apr 2
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol100183s

Cite this

@article{83a7c48a96094625bfbd4a23a82e3fe4,

title = "Catalytic asymmetric conjugate addition of α-cyanoketones for the construction of a quaternary stereogenic center",

abstract = "(Figure Presented) The catalytic asymmetric conjugate addition of a-cyanoketone pronucleophiles to vinyl ketones promoted by a Y/1 catalyst is described. High enantioselectivity was observed for a range of aromatic vinyl ketones, providing 1,5-dicarbonyl compounds bearing an all-carbon quaternary stereogenic center. The product was successfully converted to a spiro-piperidine entity and a bicyclo[3.3.0]octane framework through either the reduction of nitrile or intramolecular pinacol coupling.",

author = "Yuji Kawato and Noriko Takahashi and Naoya Kumagai and Masakatsu Shibasaki",

year = "2010",

month = apr,

day = "2",

doi = "10.1021/ol100183s",

language = "English",

volume = "12",

pages = "1484--1487",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "7",

}

TY - JOUR

T1 - Catalytic asymmetric conjugate addition of α-cyanoketones for the construction of a quaternary stereogenic center

AU - Kawato, Yuji

AU - Takahashi, Noriko

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

PY - 2010/4/2

Y1 - 2010/4/2

N2 - (Figure Presented) The catalytic asymmetric conjugate addition of a-cyanoketone pronucleophiles to vinyl ketones promoted by a Y/1 catalyst is described. High enantioselectivity was observed for a range of aromatic vinyl ketones, providing 1,5-dicarbonyl compounds bearing an all-carbon quaternary stereogenic center. The product was successfully converted to a spiro-piperidine entity and a bicyclo[3.3.0]octane framework through either the reduction of nitrile or intramolecular pinacol coupling.

AB - (Figure Presented) The catalytic asymmetric conjugate addition of a-cyanoketone pronucleophiles to vinyl ketones promoted by a Y/1 catalyst is described. High enantioselectivity was observed for a range of aromatic vinyl ketones, providing 1,5-dicarbonyl compounds bearing an all-carbon quaternary stereogenic center. The product was successfully converted to a spiro-piperidine entity and a bicyclo[3.3.0]octane framework through either the reduction of nitrile or intramolecular pinacol coupling.

UR - http://www.scopus.com/inward/record.url?scp=77950233676&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77950233676&partnerID=8YFLogxK

U2 - 10.1021/ol100183s

DO - 10.1021/ol100183s

M3 - Article

C2 - 20201564

AN - SCOPUS:77950233676

SN - 1523-7060

VL - 12

SP - 1484

EP - 1487

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Catalytic asymmetric conjugate addition of α-cyanoketones for the construction of a quaternary stereogenic center

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this