Diastereoselective cobalt-catalyzed alkylative aldol cyclizations using trialkylaluminum reagents

Mairi E. Rudkin; Pekka M. Joensuu; William S. MacLachlan; Hon Wai Lam

doi:10.1021/ol800883b

Diastereoselective cobalt-catalyzed alkylative aldol cyclizations using trialkylaluminum reagents

Mairi E. Rudkin, Pekka M. Joensuu, William S. MacLachlan, Hon Wai Lam

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

Abstract / Description of output

Co(acac)(2)center dot 2H(2)O serves as an effective precatalyst for alkylative aldol cyclizations of alpha,beta-unsaturated amides with ketones using trialkylaluminum reagents. These reactions provide beta-hydroxylactams containing three contiguous stereocenters with high levels of diastereoselection.

Original language	English
Pages (from-to)	2939-2942
Number of pages	4
Journal	Organic letters
Volume	10
Issue number	14
DOIs	https://doi.org/10.1021/ol800883b
Publication status	Published - 17 Jul 2008

Keywords / Materials (for Non-textual outputs)

TANDEM CONJUGATE ADDITION
ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
1,4-ADDITION-ALDOL REACTION
ENANTIOSELECTIVE SYNTHESIS
STOICHIOMETRIC REDUCTANT
KETONES
ENONES
TRIMETHYLALUMINUM
DIETHYLZINC
TRANSFORMATIONS

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10.1021/ol800883b

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@article{57f43754993143919489f9c57a6d27ac,

title = "Diastereoselective cobalt-catalyzed alkylative aldol cyclizations using trialkylaluminum reagents",

abstract = "Co(acac)(2)center dot 2H(2)O serves as an effective precatalyst for alkylative aldol cyclizations of alpha,beta-unsaturated amides with ketones using trialkylaluminum reagents. These reactions provide beta-hydroxylactams containing three contiguous stereocenters with high levels of diastereoselection.",

keywords = "TANDEM CONJUGATE ADDITION, ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS, 1,4-ADDITION-ALDOL REACTION, ENANTIOSELECTIVE SYNTHESIS, STOICHIOMETRIC REDUCTANT, KETONES, ENONES, TRIMETHYLALUMINUM, DIETHYLZINC, TRANSFORMATIONS",

author = "Rudkin, {Mairi E.} and Joensuu, {Pekka M.} and MacLachlan, {William S.} and Lam, {Hon Wai}",

year = "2008",

month = jul,

day = "17",

doi = "10.1021/ol800883b",

language = "English",

volume = "10",

pages = "2939--2942",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

T1 - Diastereoselective cobalt-catalyzed alkylative aldol cyclizations using trialkylaluminum reagents

AU - Rudkin, Mairi E.

AU - Joensuu, Pekka M.

AU - MacLachlan, William S.

AU - Lam, Hon Wai

PY - 2008/7/17

Y1 - 2008/7/17

N2 - Co(acac)(2)center dot 2H(2)O serves as an effective precatalyst for alkylative aldol cyclizations of alpha,beta-unsaturated amides with ketones using trialkylaluminum reagents. These reactions provide beta-hydroxylactams containing three contiguous stereocenters with high levels of diastereoselection.

AB - Co(acac)(2)center dot 2H(2)O serves as an effective precatalyst for alkylative aldol cyclizations of alpha,beta-unsaturated amides with ketones using trialkylaluminum reagents. These reactions provide beta-hydroxylactams containing three contiguous stereocenters with high levels of diastereoselection.

KW - TANDEM CONJUGATE ADDITION

KW - ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS

KW - 1,4-ADDITION-ALDOL REACTION

KW - ENANTIOSELECTIVE SYNTHESIS

KW - STOICHIOMETRIC REDUCTANT

KW - KETONES

KW - ENONES

KW - TRIMETHYLALUMINUM

KW - DIETHYLZINC

KW - TRANSFORMATIONS

UR - http://www.scopus.com/inward/record.url?scp=52049112610&partnerID=8YFLogxK

U2 - 10.1021/ol800883b

DO - 10.1021/ol800883b

M3 - Article

SN - 1523-7060

VL - 10

SP - 2939

EP - 2942

JO - Organic letters

JF - Organic letters

IS - 14

ER -

Diastereoselective cobalt-catalyzed alkylative aldol cyclizations using trialkylaluminum reagents

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Keywords / Materials (for Non-textual outputs)

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