Synthesis of highly functionalized 2,5-disubstituted pyrrolidines via an aza-Morita-Baylis-Hillman-type reaction

James E. Kitulagoda; Anders Palmelund; Varinder K. Aggarwal

doi:10.1016/j.tet.2010.05.047

Synthesis of highly functionalized 2,5-disubstituted pyrrolidines via an aza-Morita-Baylis-Hillman-type reaction

James E. Kitulagoda, Anders Palmelund, Varinder K. Aggarwal^*

^*Corresponding author for this work

School of Chemistry

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

16 Citations (Scopus)

Abstract

An aza-Morita-Baylis-Hillman-type reaction of Michael acceptors with 5-substituted cyclic N,O-acetals derived from pyrrolidines has been investigated. It has been found that the combination of Me(2)S and TMSOTf work well with unhindered and reactive enals and enones whilst the use of quinuclidine and TMSOTf is superior for more hindered Michael acceptors. The reactions lead to 2,5-trans-disubstituted pyrrolidines with good to excellent diastereoselectivity. The origin of the selectivity is discussed. (C) 2010 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	6293-6299
Number of pages	7
Journal	Tetrahedron
Volume	66
Issue number	33
DOIs	https://doi.org/10.1016/j.tet.2010.05.047
Publication status	Published - 14 Aug 2010
Event	10th Tetrahedron Symposium on Challenges in Organic and Bioorganic Chemistry - Paris, France Duration: 23 Jun 2009 → 26 Jun 2009

Research Groups and Themes

Organic & Biological

Keywords

N-ACYLIMINIUM IONS
D-RING FRAGMENTS
TRANS-2,5-DISUBSTITUTED PYRROLIDINES
ASYMMETRIC INDUCTION
CHIRAL AUXILIARIES
ENANTIOSELECTIVE SYNTHESIS
ELECTROCHEMICAL OXIDATION
STEREOSELECTIVE ADDITION
CLAISEN REARRANGEMENTS
ORGANOCOPPER REAGENTS

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10.1016/j.tet.2010.05.047

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NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS
Aggarwal, V. K. (Principal Investigator)
1/10/05 → 1/10/10
Project: Research

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title = "Synthesis of highly functionalized 2,5-disubstituted pyrrolidines via an aza-Morita-Baylis-Hillman-type reaction",

abstract = "An aza-Morita-Baylis-Hillman-type reaction of Michael acceptors with 5-substituted cyclic N,O-acetals derived from pyrrolidines has been investigated. It has been found that the combination of Me(2)S and TMSOTf work well with unhindered and reactive enals and enones whilst the use of quinuclidine and TMSOTf is superior for more hindered Michael acceptors. The reactions lead to 2,5-trans-disubstituted pyrrolidines with good to excellent diastereoselectivity. The origin of the selectivity is discussed. (C) 2010 Elsevier Ltd. All rights reserved.",

keywords = "N-ACYLIMINIUM IONS, D-RING FRAGMENTS, TRANS-2,5-DISUBSTITUTED PYRROLIDINES, ASYMMETRIC INDUCTION, CHIRAL AUXILIARIES, ENANTIOSELECTIVE SYNTHESIS, ELECTROCHEMICAL OXIDATION, STEREOSELECTIVE ADDITION, CLAISEN REARRANGEMENTS, ORGANOCOPPER REAGENTS",

author = "Kitulagoda, \{James E.\} and Anders Palmelund and Aggarwal, \{Varinder K.\}",

year = "2010",

month = aug,

day = "14",

doi = "10.1016/j.tet.2010.05.047",

language = "English",

volume = "66",

pages = "6293--6299",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "33",

note = "10th Tetrahedron Symposium on Challenges in Organic and Bioorganic Chemistry ; Conference date: 23-06-2009 Through 26-06-2009",

}

TY - JOUR

T1 - Synthesis of highly functionalized 2,5-disubstituted pyrrolidines via an aza-Morita-Baylis-Hillman-type reaction

AU - Kitulagoda, James E.

AU - Palmelund, Anders

AU - Aggarwal, Varinder K.

PY - 2010/8/14

Y1 - 2010/8/14

N2 - An aza-Morita-Baylis-Hillman-type reaction of Michael acceptors with 5-substituted cyclic N,O-acetals derived from pyrrolidines has been investigated. It has been found that the combination of Me(2)S and TMSOTf work well with unhindered and reactive enals and enones whilst the use of quinuclidine and TMSOTf is superior for more hindered Michael acceptors. The reactions lead to 2,5-trans-disubstituted pyrrolidines with good to excellent diastereoselectivity. The origin of the selectivity is discussed. (C) 2010 Elsevier Ltd. All rights reserved.

AB - An aza-Morita-Baylis-Hillman-type reaction of Michael acceptors with 5-substituted cyclic N,O-acetals derived from pyrrolidines has been investigated. It has been found that the combination of Me(2)S and TMSOTf work well with unhindered and reactive enals and enones whilst the use of quinuclidine and TMSOTf is superior for more hindered Michael acceptors. The reactions lead to 2,5-trans-disubstituted pyrrolidines with good to excellent diastereoselectivity. The origin of the selectivity is discussed. (C) 2010 Elsevier Ltd. All rights reserved.

KW - N-ACYLIMINIUM IONS

KW - D-RING FRAGMENTS

KW - TRANS-2,5-DISUBSTITUTED PYRROLIDINES

KW - ASYMMETRIC INDUCTION

KW - CHIRAL AUXILIARIES

KW - ENANTIOSELECTIVE SYNTHESIS

KW - ELECTROCHEMICAL OXIDATION

KW - STEREOSELECTIVE ADDITION

KW - CLAISEN REARRANGEMENTS

KW - ORGANOCOPPER REAGENTS

U2 - 10.1016/j.tet.2010.05.047

DO - 10.1016/j.tet.2010.05.047

M3 - Article (Academic Journal)

SN - 0040-4020

VL - 66

SP - 6293

EP - 6299

JO - Tetrahedron

JF - Tetrahedron

IS - 33

T2 - 10th Tetrahedron Symposium on Challenges in Organic and Bioorganic Chemistry

Y2 - 23 June 2009 through 26 June 2009

ER -

Synthesis of highly functionalized 2,5-disubstituted pyrrolidines via an aza-Morita-Baylis-Hillman-type reaction

Abstract

Research Groups and Themes

Keywords

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Projects

NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS

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