Reactions of iminium ions with Michael acceptors through a Morita-Baylis-Hillman-type reaction: Enantiocontrol and applications in synthesis

Eddie L. Myers; Johannes G. De Vries; Varinder K. Aggarwal

doi:10.1002/anie.200604715

Reactions of iminium ions with Michael acceptors through a Morita-Baylis-Hillman-type reaction: Enantiocontrol and applications in synthesis

Eddie L. Myers, Johannes G. De Vries, Varinder K. Aggarwal

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

87 Citations (Scopus)

Abstract

(Chemical Equation Presented) All adducts one way: Iminium ions, generated in situ from the corresponding N,O-acetals, can be used as electrophiles in a Morita-Baylis-Hillman-type reaction with a wide range of Michael acceptors (enones, enals, S- and O-acrylates). The reaction has been rendered asymmetric using sulfide 1 (see scheme; DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene, TMSOTf=trimethylsilyl trifluoromethanesulfonate).

Original language	English
Pages (from-to)	1893-1896
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	11
DOIs	https://doi.org/10.1002/anie.200604715
Publication status	Published - 2007
Externally published	Yes

Keywords

C-C coupling
Lewis acids
Lewis bases
Mannich reaction
Morita-Baylis-Hillman reaction

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10.1002/anie.200604715

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title = "Reactions of iminium ions with Michael acceptors through a Morita-Baylis-Hillman-type reaction: Enantiocontrol and applications in synthesis",

abstract = "(Chemical Equation Presented) All adducts one way: Iminium ions, generated in situ from the corresponding N,O-acetals, can be used as electrophiles in a Morita-Baylis-Hillman-type reaction with a wide range of Michael acceptors (enones, enals, S- and O-acrylates). The reaction has been rendered asymmetric using sulfide 1 (see scheme; DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene, TMSOTf=trimethylsilyl trifluoromethanesulfonate).",

keywords = "C-C coupling, Lewis acids, Lewis bases, Mannich reaction, Morita-Baylis-Hillman reaction",

author = "Myers, \{Eddie L.\} and \{De Vries\}, \{Johannes G.\} and Aggarwal, \{Varinder K.\}",

year = "2007",

doi = "10.1002/anie.200604715",

language = "English",

volume = "46",

pages = "1893--1896",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "11",

}

Reactions of iminium ions with Michael acceptors through a Morita-Baylis-Hillman-type reaction: Enantiocontrol and applications in synthesis. / Myers, Eddie L.; De Vries, Johannes G.; Aggarwal, Varinder K.
In: Angewandte Chemie - International Edition, Vol. 46, No. 11, 2007, p. 1893-1896.

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

TY - JOUR

T1 - Reactions of iminium ions with Michael acceptors through a Morita-Baylis-Hillman-type reaction

T2 - Enantiocontrol and applications in synthesis

AU - Myers, Eddie L.

AU - De Vries, Johannes G.

AU - Aggarwal, Varinder K.

PY - 2007

Y1 - 2007

N2 - (Chemical Equation Presented) All adducts one way: Iminium ions, generated in situ from the corresponding N,O-acetals, can be used as electrophiles in a Morita-Baylis-Hillman-type reaction with a wide range of Michael acceptors (enones, enals, S- and O-acrylates). The reaction has been rendered asymmetric using sulfide 1 (see scheme; DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene, TMSOTf=trimethylsilyl trifluoromethanesulfonate).

AB - (Chemical Equation Presented) All adducts one way: Iminium ions, generated in situ from the corresponding N,O-acetals, can be used as electrophiles in a Morita-Baylis-Hillman-type reaction with a wide range of Michael acceptors (enones, enals, S- and O-acrylates). The reaction has been rendered asymmetric using sulfide 1 (see scheme; DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene, TMSOTf=trimethylsilyl trifluoromethanesulfonate).

KW - C-C coupling

KW - Lewis acids

KW - Lewis bases

KW - Mannich reaction

KW - Morita-Baylis-Hillman reaction

UR - https://www.scopus.com/pages/publications/34249688755

U2 - 10.1002/anie.200604715

DO - 10.1002/anie.200604715

M3 - Article

SN - 1433-7851

VL - 46

SP - 1893

EP - 1896

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 11

ER -

Reactions of iminium ions with Michael acceptors through a Morita-Baylis-Hillman-type reaction: Enantiocontrol and applications in synthesis

Abstract

Keywords

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