Organocatalytic synthesis of multiple substituted b[4.4.0]decalin system

Shaik Anwar; Hui Ju Chang; Kwunmin Chen

doi:10.1021/ol200424x

Organocatalytic synthesis of multiple substituted b[4.4.0]decalin system

Shaik Anwar, Hui Ju Chang, Kwunmin Chen^*

^*Corresponding author for this work

Department of Chemistry

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

40 Citations (Scopus)

Abstract

Chemical equations presented. An efficient and unprecedented organocatalytic reaction of γ-nitroketones with α,β-unsaturated aldehydes to give polyfunctionalized [4.4.0] bicyclic skeletons was developed. The diphenylprolinol silyl ether mediated nitro-Michael/Aldol reaction afforded the hexa-substituted decalin carboaldehydes with excellent diastereo- and enantioselectivity (up to >99:1 dr and >99% ee) via a formal [4 + 2] carbocyclization process.

Original language	English
Pages (from-to)	2200-2203
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	9
DOIs	https://doi.org/10.1021/ol200424x
Publication status	Published - 2011 May 6

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol200424x

Cite this

@article{f820a44ecc494d16a15aaa92d897d917,

title = "Organocatalytic synthesis of multiple substituted b[4.4.0]decalin system",

abstract = "Chemical equations presented. An efficient and unprecedented organocatalytic reaction of γ-nitroketones with α,β-unsaturated aldehydes to give polyfunctionalized [4.4.0] bicyclic skeletons was developed. The diphenylprolinol silyl ether mediated nitro-Michael/Aldol reaction afforded the hexa-substituted decalin carboaldehydes with excellent diastereo- and enantioselectivity (up to >99:1 dr and >99% ee) via a formal [4 + 2] carbocyclization process.",

author = "Shaik Anwar and Chang, {Hui Ju} and Kwunmin Chen",

year = "2011",

month = may,

day = "6",

doi = "10.1021/ol200424x",

language = "English",

volume = "13",

pages = "2200--2203",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Organocatalytic synthesis of multiple substituted b[4.4.0]decalin system

AU - Anwar, Shaik

AU - Chang, Hui Ju

AU - Chen, Kwunmin

PY - 2011/5/6

Y1 - 2011/5/6

N2 - Chemical equations presented. An efficient and unprecedented organocatalytic reaction of γ-nitroketones with α,β-unsaturated aldehydes to give polyfunctionalized [4.4.0] bicyclic skeletons was developed. The diphenylprolinol silyl ether mediated nitro-Michael/Aldol reaction afforded the hexa-substituted decalin carboaldehydes with excellent diastereo- and enantioselectivity (up to >99:1 dr and >99% ee) via a formal [4 + 2] carbocyclization process.

AB - Chemical equations presented. An efficient and unprecedented organocatalytic reaction of γ-nitroketones with α,β-unsaturated aldehydes to give polyfunctionalized [4.4.0] bicyclic skeletons was developed. The diphenylprolinol silyl ether mediated nitro-Michael/Aldol reaction afforded the hexa-substituted decalin carboaldehydes with excellent diastereo- and enantioselectivity (up to >99:1 dr and >99% ee) via a formal [4 + 2] carbocyclization process.

UR - http://www.scopus.com/inward/record.url?scp=79955599615&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79955599615&partnerID=8YFLogxK

U2 - 10.1021/ol200424x

DO - 10.1021/ol200424x

M3 - Article

C2 - 21476516

AN - SCOPUS:79955599615

VL - 13

SP - 2200

EP - 2203

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 9

ER -

Organocatalytic synthesis of multiple substituted b[4.4.0]decalin system

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 805805: Experimental Crystal Structure Determination

CCDC 806842: Experimental Crystal Structure Determination

Cite this

Organocatalytic synthesis of multiple substituted b[4.4.0]decalin system

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 805805: Experimental Crystal Structure Determination

CCDC 806842: Experimental Crystal Structure Determination

Cite this