Diastereoselective cobalt-catalyzed reductive aldol cyclizations using diethylzinc as the stoichiometric reductant

Hon Wai Lam; Pekka M. Joensuu; Gordon J. Murray; Euan A. F. Fordyce; Oscar Prieto; Thomas Luebbers

doi:10.1021/ol061329d

Diastereoselective cobalt-catalyzed reductive aldol cyclizations using diethylzinc as the stoichiometric reductant

Hon Wai Lam, Pekka M. Joensuu, Gordon J. Murray, Euan A. F. Fordyce, Oscar Prieto, Thomas Luebbers

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

Abstract

Cobalt catalysis enables a new method for the generation of zinc enolates using diethylzinc to reduce alpha,ss-unsaturated amides. This method has been applied to a high-yielding diastereoselective reductive aldol cyclization.

Original language	English
Pages (from-to)	3729-3732
Number of pages	4
Journal	Organic letters
Volume	8
Issue number	17
DOIs	https://doi.org/10.1021/ol061329d
Publication status	Published - 17 Aug 2006

Keywords / Materials (for Non-textual outputs)

REFORMATSKY-TYPE REACTION
ALPHA,BETA-UNSATURATED CARBOXAMIDES
ENANTIOSELECTIVE SYNTHESIS
KETONES
ALKYNES
ALPHA
CYCLOREDUCTIONS
HOMOALLYLATION
1,4-REDUCTION
HYDROGENATION

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10.1021/ol061329d

1 , 3-Dipolar Cycloaddition Approaches to functionalised Gamma-Lactams and Pyroglutamic Acids
Lam, H. (Principal Investigator)
EPSRC
4/04/05 → 30/09/07
Project: Research

Cite this

@article{75bd111c2ddb4a52b20c97491ad09983,

title = "Diastereoselective cobalt-catalyzed reductive aldol cyclizations using diethylzinc as the stoichiometric reductant",

abstract = "Cobalt catalysis enables a new method for the generation of zinc enolates using diethylzinc to reduce alpha,ss-unsaturated amides. This method has been applied to a high-yielding diastereoselective reductive aldol cyclization.",

keywords = "REFORMATSKY-TYPE REACTION, ALPHA,BETA-UNSATURATED CARBOXAMIDES, ENANTIOSELECTIVE SYNTHESIS, KETONES, ALKYNES, ALPHA, CYCLOREDUCTIONS, HOMOALLYLATION, 1,4-REDUCTION, HYDROGENATION",

author = "Lam, \{Hon Wai\} and Joensuu, \{Pekka M.\} and Murray, \{Gordon J.\} and Fordyce, \{Euan A. F.\} and Oscar Prieto and Thomas Luebbers",

year = "2006",

month = aug,

day = "17",

doi = "10.1021/ol061329d",

language = "English",

volume = "8",

pages = "3729--3732",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - Diastereoselective cobalt-catalyzed reductive aldol cyclizations using diethylzinc as the stoichiometric reductant

AU - Lam, Hon Wai

AU - Joensuu, Pekka M.

AU - Murray, Gordon J.

AU - Fordyce, Euan A. F.

AU - Prieto, Oscar

AU - Luebbers, Thomas

PY - 2006/8/17

Y1 - 2006/8/17

N2 - Cobalt catalysis enables a new method for the generation of zinc enolates using diethylzinc to reduce alpha,ss-unsaturated amides. This method has been applied to a high-yielding diastereoselective reductive aldol cyclization.

AB - Cobalt catalysis enables a new method for the generation of zinc enolates using diethylzinc to reduce alpha,ss-unsaturated amides. This method has been applied to a high-yielding diastereoselective reductive aldol cyclization.

KW - REFORMATSKY-TYPE REACTION

KW - ALPHA,BETA-UNSATURATED CARBOXAMIDES

KW - ENANTIOSELECTIVE SYNTHESIS

KW - KETONES

KW - ALKYNES

KW - ALPHA

KW - CYCLOREDUCTIONS

KW - HOMOALLYLATION

KW - 1,4-REDUCTION

KW - HYDROGENATION

U2 - 10.1021/ol061329d

DO - 10.1021/ol061329d

M3 - Article

SN - 1523-7060

VL - 8

SP - 3729

EP - 3732

JO - Organic letters

JF - Organic letters

IS - 17

ER -

Diastereoselective cobalt-catalyzed reductive aldol cyclizations using diethylzinc as the stoichiometric reductant

Abstract

Keywords / Materials (for Non-textual outputs)

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Projects

1 , 3-Dipolar Cycloaddition Approaches to functionalised Gamma-Lactams and Pyroglutamic Acids

Cite this