Diastereoselective intermolecular cobalt-catalyzed reductive aldol reactions of alpha,beta-unsaturated Amides with ketones

Ralph J. R. Lumby; Pekka M. Joensuu; Hon Wai Lam

doi:10.1021/o1701980e

Diastereoselective intermolecular cobalt-catalyzed reductive aldol reactions of alpha,beta-unsaturated Amides with ketones

Ralph J. R. Lumby, Pekka M. Joensuu, Hon Wai Lam

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

Abstract

Under cobalt catalysis, diethylzinc mediates the conjugate reduction of alpha,beta-unsaturated amides to produce ethylzinc enolates that react with ketones in situ to produce tertiary alcohol-containing aldol products with up to >19:1 diastereoselectivity.

Original language	English
Pages (from-to)	4367-4370
Number of pages	4
Journal	Organic letters
Volume	9
Issue number	21
DOIs	https://doi.org/10.1021/o1701980e
Publication status	Published - 11 Oct 2007

Keywords / Materials (for Non-textual outputs)

ENANTIOSELECTIVE CONJUGATE ADDITION
ASYMMETRIC ZN CATALYSIS
DINUCLEAR ZINC CATALYST
MANNICH-TYPE REACTION
REFORMATSKY REACTION
ET2ZN/LINKED-BINOL COMPLEX
ALPHA-ARYLATION
BETA-AMINO
ORGANOZINC REAGENTS
ORGANIC-SYNTHESIS

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@article{990e9e5c1b454b7f9c85f3f329f1721d,

title = "Diastereoselective intermolecular cobalt-catalyzed reductive aldol reactions of alpha,beta-unsaturated Amides with ketones",

abstract = "Under cobalt catalysis, diethylzinc mediates the conjugate reduction of alpha,beta-unsaturated amides to produce ethylzinc enolates that react with ketones in situ to produce tertiary alcohol-containing aldol products with up to >19:1 diastereoselectivity.",

keywords = "ENANTIOSELECTIVE CONJUGATE ADDITION, ASYMMETRIC ZN CATALYSIS, DINUCLEAR ZINC CATALYST, MANNICH-TYPE REACTION, REFORMATSKY REACTION, ET2ZN/LINKED-BINOL COMPLEX, ALPHA-ARYLATION, BETA-AMINO, ORGANOZINC REAGENTS, ORGANIC-SYNTHESIS",

author = "Lumby, \{Ralph J. R.\} and Joensuu, \{Pekka M.\} and Lam, \{Hon Wai\}",

year = "2007",

month = oct,

day = "11",

doi = "10.1021/o1701980e",

language = "English",

volume = "9",

pages = "4367--4370",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Diastereoselective intermolecular cobalt-catalyzed reductive aldol reactions of alpha,beta-unsaturated Amides with ketones

AU - Lumby, Ralph J. R.

AU - Joensuu, Pekka M.

AU - Lam, Hon Wai

PY - 2007/10/11

Y1 - 2007/10/11

N2 - Under cobalt catalysis, diethylzinc mediates the conjugate reduction of alpha,beta-unsaturated amides to produce ethylzinc enolates that react with ketones in situ to produce tertiary alcohol-containing aldol products with up to >19:1 diastereoselectivity.

AB - Under cobalt catalysis, diethylzinc mediates the conjugate reduction of alpha,beta-unsaturated amides to produce ethylzinc enolates that react with ketones in situ to produce tertiary alcohol-containing aldol products with up to >19:1 diastereoselectivity.

KW - ENANTIOSELECTIVE CONJUGATE ADDITION

KW - ASYMMETRIC ZN CATALYSIS

KW - DINUCLEAR ZINC CATALYST

KW - MANNICH-TYPE REACTION

KW - REFORMATSKY REACTION

KW - ET2ZN/LINKED-BINOL COMPLEX

KW - ALPHA-ARYLATION

KW - BETA-AMINO

KW - ORGANOZINC REAGENTS

KW - ORGANIC-SYNTHESIS

U2 - 10.1021/o1701980e

DO - 10.1021/o1701980e

M3 - Article

SN - 1523-7060

VL - 9

SP - 4367

EP - 4370

JO - Organic letters

JF - Organic letters

IS - 21

ER -

Diastereoselective intermolecular cobalt-catalyzed reductive aldol reactions of alpha,beta-unsaturated Amides with ketones

Abstract

Keywords / Materials (for Non-textual outputs)

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