Catalytic asymmetric construction of spiro(γ-butyrolactam-γ- butyrolactone) moieties through sequential reactions of cyclic imino esters with Morita-Baylis-Hillman bromides

Huai Long Teng; He Huang; Chun Jiang Wang

doi:10.1002/chem.201201475

Catalytic asymmetric construction of spiro(γ-butyrolactam-γ- butyrolactone) moieties through sequential reactions of cyclic imino esters with Morita-Baylis-Hillman bromides

Huai Long Teng
, He Huang
, Chun Jiang Wang^*

^*Corresponding author for this work

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

46 Citations (Scopus)

Abstract

Spiro(γ-butyrolactam-γ-butyrolactone): A route to enantioenriched spiro(γ-butyrolactam-γ-butyrolactone) compounds, a valuable motif for drug discovery, was developed by use of a highly efficient copper(I)/TF-BiphamPhos-catalyzed tandem Michael addition-elimination of homoserine lactone derived cyclic imino esters with Morita-Baylis-Hillman (MBH) bromides, followed by treatment with para-toluenesulfonic acid (see scheme).

Original language	English
Pages (from-to)	12614-12618
Number of pages	5
Journal	Chemistry - A European Journal
Volume	18
Issue number	40
DOIs	https://doi.org/10.1002/chem.201201475
Publication status	Published - 1 Oct 2012
Externally published	Yes

Keywords

asymmetric catalysis
bromides
diastereoselectivity
enantioselectivity
imino esters
spiro compounds

Access to Document

10.1002/chem.201201475

Cite this

@article{a6568c714c754b14bd35b7cfe788b3b0,

title = "Catalytic asymmetric construction of spiro(γ-butyrolactam-γ- butyrolactone) moieties through sequential reactions of cyclic imino esters with Morita-Baylis-Hillman bromides",

abstract = "Spiro(γ-butyrolactam-γ-butyrolactone): A route to enantioenriched spiro(γ-butyrolactam-γ-butyrolactone) compounds, a valuable motif for drug discovery, was developed by use of a highly efficient copper(I)/TF-BiphamPhos-catalyzed tandem Michael addition-elimination of homoserine lactone derived cyclic imino esters with Morita-Baylis-Hillman (MBH) bromides, followed by treatment with para-toluenesulfonic acid (see scheme).",

keywords = "asymmetric catalysis, bromides, diastereoselectivity, enantioselectivity, imino esters, spiro compounds",

author = "Teng, \{Huai Long\} and He Huang and Wang, \{Chun Jiang\}",

year = "2012",

month = oct,

day = "1",

doi = "10.1002/chem.201201475",

language = "English",

volume = "18",

pages = "12614--12618",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley and Sons Inc.",

number = "40",

}

Catalytic asymmetric construction of spiro(γ-butyrolactam-γ- butyrolactone) moieties through sequential reactions of cyclic imino esters with Morita-Baylis-Hillman bromides. / Teng, Huai Long; Huang, He; Wang, Chun Jiang.
In: Chemistry - A European Journal, Vol. 18, No. 40, 01.10.2012, p. 12614-12618.

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

TY - JOUR

T1 - Catalytic asymmetric construction of spiro(γ-butyrolactam-γ- butyrolactone) moieties through sequential reactions of cyclic imino esters with Morita-Baylis-Hillman bromides

AU - Teng, Huai Long

AU - Huang, He

AU - Wang, Chun Jiang

PY - 2012/10/1

Y1 - 2012/10/1

N2 - Spiro(γ-butyrolactam-γ-butyrolactone): A route to enantioenriched spiro(γ-butyrolactam-γ-butyrolactone) compounds, a valuable motif for drug discovery, was developed by use of a highly efficient copper(I)/TF-BiphamPhos-catalyzed tandem Michael addition-elimination of homoserine lactone derived cyclic imino esters with Morita-Baylis-Hillman (MBH) bromides, followed by treatment with para-toluenesulfonic acid (see scheme).

AB - Spiro(γ-butyrolactam-γ-butyrolactone): A route to enantioenriched spiro(γ-butyrolactam-γ-butyrolactone) compounds, a valuable motif for drug discovery, was developed by use of a highly efficient copper(I)/TF-BiphamPhos-catalyzed tandem Michael addition-elimination of homoserine lactone derived cyclic imino esters with Morita-Baylis-Hillman (MBH) bromides, followed by treatment with para-toluenesulfonic acid (see scheme).

KW - asymmetric catalysis

KW - bromides

KW - diastereoselectivity

KW - enantioselectivity

KW - imino esters

KW - spiro compounds

UR - https://www.scopus.com/pages/publications/84867081674

U2 - 10.1002/chem.201201475

DO - 10.1002/chem.201201475

M3 - Article

C2 - 22927370

AN - SCOPUS:84867081674

SN - 0947-6539

VL - 18

SP - 12614

EP - 12618

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 40

ER -

Catalytic asymmetric construction of spiro(γ-butyrolactam-γ- butyrolactone) moieties through sequential reactions of cyclic imino esters with Morita-Baylis-Hillman bromides

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this