Catalytic enantioselective henry reactions of isatins: Application in the concise synthesis of (S)-(-)-spirobrassinin

Lu Liu; Shilei Zhang; Fei Xue; Guangshun Lou; Haoyi Zhang; Shichao Ma; Wenhu Duan; Wei Wang

doi:10.1002/chem.201101025

Catalytic enantioselective henry reactions of isatins: Application in the concise synthesis of (S)-(-)-spirobrassinin

Lu Liu, Shilei Zhang, Fei Xue, Guangshun Lou, Haoyi Zhang, Shichao Ma, Wenhu Duan, Wei Wang

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

108 Scopus citations

Abstract

When isatin a cat! A highly efficient, cupreine-catalyzed, enantioselective Henry reaction of readily available isatins and nitroalkanes has been developed (see scheme). The products are produced in excellent yields and good enantioselectivities under mild reaction conditions and without chromatography. The utility of the strategy has been demonstrated in the facile synthesis of (S)-(-)-spirobrassinin without the need for protecting groups.

Original language	English (US)
Pages (from-to)	7791-7795
Number of pages	5
Journal	Chemistry - A European Journal
Volume	17
Issue number	28
DOIs	https://doi.org/10.1002/chem.201101025
State	Published - Jul 4 2011
Externally published	Yes

Keywords

Henry reaction
isatins
natural products
organocatalysis
oxindoles

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/chem.201101025

Cite this

@article{b50d6180ba5c483a9413554e9b1eb2b3,

title = "Catalytic enantioselective henry reactions of isatins: Application in the concise synthesis of (S)-(-)-spirobrassinin",

abstract = "When isatin a cat! A highly efficient, cupreine-catalyzed, enantioselective Henry reaction of readily available isatins and nitroalkanes has been developed (see scheme). The products are produced in excellent yields and good enantioselectivities under mild reaction conditions and without chromatography. The utility of the strategy has been demonstrated in the facile synthesis of (S)-(-)-spirobrassinin without the need for protecting groups.",

keywords = "Henry reaction, isatins, natural products, organocatalysis, oxindoles",

author = "Lu Liu and Shilei Zhang and Fei Xue and Guangshun Lou and Haoyi Zhang and Shichao Ma and Wenhu Duan and Wei Wang",

year = "2011",

month = jul,

day = "4",

doi = "10.1002/chem.201101025",

language = "English (US)",

volume = "17",

pages = "7791--7795",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "28",

}

TY - JOUR

T1 - Catalytic enantioselective henry reactions of isatins

T2 - Application in the concise synthesis of (S)-(-)-spirobrassinin

AU - Liu, Lu

AU - Zhang, Shilei

AU - Xue, Fei

AU - Lou, Guangshun

AU - Zhang, Haoyi

AU - Ma, Shichao

AU - Duan, Wenhu

AU - Wang, Wei

PY - 2011/7/4

Y1 - 2011/7/4

N2 - When isatin a cat! A highly efficient, cupreine-catalyzed, enantioselective Henry reaction of readily available isatins and nitroalkanes has been developed (see scheme). The products are produced in excellent yields and good enantioselectivities under mild reaction conditions and without chromatography. The utility of the strategy has been demonstrated in the facile synthesis of (S)-(-)-spirobrassinin without the need for protecting groups.

AB - When isatin a cat! A highly efficient, cupreine-catalyzed, enantioselective Henry reaction of readily available isatins and nitroalkanes has been developed (see scheme). The products are produced in excellent yields and good enantioselectivities under mild reaction conditions and without chromatography. The utility of the strategy has been demonstrated in the facile synthesis of (S)-(-)-spirobrassinin without the need for protecting groups.

KW - Henry reaction

KW - isatins

KW - natural products

KW - organocatalysis

KW - oxindoles

UR - http://www.scopus.com/inward/record.url?scp=79959681231&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79959681231&partnerID=8YFLogxK

U2 - 10.1002/chem.201101025

DO - 10.1002/chem.201101025

M3 - Article

C2 - 21626595

AN - SCOPUS:79959681231

SN - 0947-6539

VL - 17

SP - 7791

EP - 7795

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 28

ER -

Catalytic enantioselective henry reactions of isatins: Application in the concise synthesis of (S)-(-)-spirobrassinin

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this