Catalytic asymmetric Michael reactions of dibenzyl malonate to α,β-unsaturated N-acylpyrroles using a La(O-iPr)3/Ph-linked-BINOL complex

So Young Park; Hiroyuki Morimoto; Shigeki Matsunaga; Masakatsu Shibasaki

doi:10.1016/j.tetlet.2007.02.112

Catalytic asymmetric Michael reactions of dibenzyl malonate to α,β-unsaturated N-acylpyrroles using a La(O-iPr)₃/Ph-linked-BINOL complex

So Young Park, Hiroyuki Morimoto, Shigeki Matsunaga, Masakatsu Shibasaki

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

38 Citations (Scopus)

Abstract

Catalytic asymmetric Michael reactions of a malonate to acyclic α,β-unsaturated N-acylpyrroles as ester equivalent acceptors are described. A La(O-iPr)₃/(S,S)-linked-BINOL complex, which is suitable for Michael addition to cyclic enones, is not suitable for acyclic α,β-unsaturated N-acylpyrroles. A new (S,S)-Ph-linked-BINOL chiral ligand was developed to improve enantioselectivity, and a La(O-iPr)₃/(S,S)-Ph-linked-BINOL complex with the addition of HFIP afforded Michael adducts in good yield and enantioselectivity (up to 96% ee).

Original language	English
Pages (from-to)	2815-2818
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	16
DOIs	https://doi.org/10.1016/j.tetlet.2007.02.112
Publication status	Published - Apr 16 2007
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Catalytic asymmetric Michael reactions of dibenzyl malonate to α,β-unsaturated N-acylpyrroles using a La(O-iPr)3/Ph-linked-BINOL complex",

abstract = "Catalytic asymmetric Michael reactions of a malonate to acyclic α,β-unsaturated N-acylpyrroles as ester equivalent acceptors are described. A La(O-iPr)3/(S,S)-linked-BINOL complex, which is suitable for Michael addition to cyclic enones, is not suitable for acyclic α,β-unsaturated N-acylpyrroles. A new (S,S)-Ph-linked-BINOL chiral ligand was developed to improve enantioselectivity, and a La(O-iPr)3/(S,S)-Ph-linked-BINOL complex with the addition of HFIP afforded Michael adducts in good yield and enantioselectivity (up to 96% ee).",

author = "Park, {So Young} and Hiroyuki Morimoto and Shigeki Matsunaga and Masakatsu Shibasaki",

note = "Funding Information: We thank financial support by Grant-in-Aid for Specially Promoted Research and Grant-in-Aid for Encouragements for Young Scientists (B) (S.M.) from JSPS and MEXT. H.M. thanks JSPS Research Fellowships for Young Scientists. We thank Mr. H. Noda and Dr. T. Yoshida for their generous supports for ligand 1b and substrates synthesis.",

year = "2007",

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doi = "10.1016/j.tetlet.2007.02.112",

language = "English",

volume = "48",

pages = "2815--2818",

journal = "Tetrahedron Letters",

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T1 - Catalytic asymmetric Michael reactions of dibenzyl malonate to α,β-unsaturated N-acylpyrroles using a La(O-iPr)3/Ph-linked-BINOL complex

AU - Park, So Young

AU - Morimoto, Hiroyuki

AU - Matsunaga, Shigeki

AU - Shibasaki, Masakatsu

N1 - Funding Information: We thank financial support by Grant-in-Aid for Specially Promoted Research and Grant-in-Aid for Encouragements for Young Scientists (B) (S.M.) from JSPS and MEXT. H.M. thanks JSPS Research Fellowships for Young Scientists. We thank Mr. H. Noda and Dr. T. Yoshida for their generous supports for ligand 1b and substrates synthesis.

PY - 2007/4/16

Y1 - 2007/4/16

N2 - Catalytic asymmetric Michael reactions of a malonate to acyclic α,β-unsaturated N-acylpyrroles as ester equivalent acceptors are described. A La(O-iPr)3/(S,S)-linked-BINOL complex, which is suitable for Michael addition to cyclic enones, is not suitable for acyclic α,β-unsaturated N-acylpyrroles. A new (S,S)-Ph-linked-BINOL chiral ligand was developed to improve enantioselectivity, and a La(O-iPr)3/(S,S)-Ph-linked-BINOL complex with the addition of HFIP afforded Michael adducts in good yield and enantioselectivity (up to 96% ee).

AB - Catalytic asymmetric Michael reactions of a malonate to acyclic α,β-unsaturated N-acylpyrroles as ester equivalent acceptors are described. A La(O-iPr)3/(S,S)-linked-BINOL complex, which is suitable for Michael addition to cyclic enones, is not suitable for acyclic α,β-unsaturated N-acylpyrroles. A new (S,S)-Ph-linked-BINOL chiral ligand was developed to improve enantioselectivity, and a La(O-iPr)3/(S,S)-Ph-linked-BINOL complex with the addition of HFIP afforded Michael adducts in good yield and enantioselectivity (up to 96% ee).

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SN - 0040-4039

VL - 48

SP - 2815

EP - 2818

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 16

ER -

Catalytic asymmetric Michael reactions of dibenzyl malonate to α,β-unsaturated N-acylpyrroles using a La(O-iPr)₃/Ph-linked-BINOL complex

Abstract

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