Enantioselective synthesis of 2-aryl-4-piperidones via rhodium/phosphoramidite-catalyzed conjugate addition of arylboroxines

R. B. C. Jagt; JG de Vries; BL Feringa; AJ Minnaard

doi:10.1021/ol050734m

Enantioselective synthesis of 2-aryl-4-piperidones via rhodium/phosphoramidite-catalyzed conjugate addition of arylboroxines

R. B. C. Jagt
, JG de Vries
, BL Feringa
, AJ Minnaard

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

63 Citations (Scopus)

Abstract

[GRAPHICS]

The highly enantioselective synthesis of 2-aryl-4-piperidones by rhodium/phosphoramidite-catalyzed conjugate addition of arylboroxines to 2,3-dihydro-4-pyridones is described. Both enantiomers of a variety of products with sterically and electronically different R substituents were obtained in high isolated yield and with excellent enantioselectivity up to 99%.

Original language	English
Pages (from-to)	2433-2435
Number of pages	3
Journal	Organic letters
Volume	7
Issue number	12
DOIs	https://doi.org/10.1021/ol050734m
Publication status	Published - 9-Jun-2005

Keywords

MONODENTATE PHOSPHORAMIDITE LIGANDS
C BOND FORMATION
ASYMMETRIC 1,4-ADDITION
ACIDS
HYDROGENATION
PIPERIDINES
REAGENTS
ENONES
NUCLEOPHILES

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title = "Enantioselective synthesis of 2-aryl-4-piperidones via rhodium/phosphoramidite-catalyzed conjugate addition of arylboroxines",

abstract = "[GRAPHICS]The highly enantioselective synthesis of 2-aryl-4-piperidones by rhodium/phosphoramidite-catalyzed conjugate addition of arylboroxines to 2,3-dihydro-4-pyridones is described. Both enantiomers of a variety of products with sterically and electronically different R substituents were obtained in high isolated yield and with excellent enantioselectivity up to 99\%.",

keywords = "MONODENTATE PHOSPHORAMIDITE LIGANDS, C BOND FORMATION, ASYMMETRIC 1,4-ADDITION, ACIDS, HYDROGENATION, PIPERIDINES, REAGENTS, ENONES, NUCLEOPHILES",

author = "Jagt, \{R. B. C.\} and \{de Vries\}, JG and BL Feringa and AJ Minnaard",

year = "2005",

month = jun,

day = "9",

doi = "10.1021/ol050734m",

language = "English",

volume = "7",

pages = "2433--2435",

journal = "Organic letters",

issn = "1523-7060",

publisher = "AMER CHEMICAL SOC INC",

number = "12",

}

TY - JOUR

T1 - Enantioselective synthesis of 2-aryl-4-piperidones via rhodium/phosphoramidite-catalyzed conjugate addition of arylboroxines

AU - Jagt, R. B. C.

AU - de Vries, JG

AU - Feringa, BL

AU - Minnaard, AJ

PY - 2005/6/9

Y1 - 2005/6/9

N2 - [GRAPHICS]The highly enantioselective synthesis of 2-aryl-4-piperidones by rhodium/phosphoramidite-catalyzed conjugate addition of arylboroxines to 2,3-dihydro-4-pyridones is described. Both enantiomers of a variety of products with sterically and electronically different R substituents were obtained in high isolated yield and with excellent enantioselectivity up to 99%.

AB - [GRAPHICS]The highly enantioselective synthesis of 2-aryl-4-piperidones by rhodium/phosphoramidite-catalyzed conjugate addition of arylboroxines to 2,3-dihydro-4-pyridones is described. Both enantiomers of a variety of products with sterically and electronically different R substituents were obtained in high isolated yield and with excellent enantioselectivity up to 99%.

KW - MONODENTATE PHOSPHORAMIDITE LIGANDS

KW - C BOND FORMATION

KW - ASYMMETRIC 1,4-ADDITION

KW - ACIDS

KW - HYDROGENATION

KW - PIPERIDINES

KW - REAGENTS

KW - ENONES

KW - NUCLEOPHILES

UR - https://www.scopus.com/pages/publications/20544440852

U2 - 10.1021/ol050734m

DO - 10.1021/ol050734m

M3 - Article

SN - 1523-7060

VL - 7

SP - 2433

EP - 2435

JO - Organic letters

JF - Organic letters

IS - 12

ER -

Enantioselective synthesis of 2-aryl-4-piperidones via rhodium/phosphoramidite-catalyzed conjugate addition of arylboroxines

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