Camphor sulfonyl hydrazines (CaSH) as organocatalysts in enantioselective Diels-Alder reactions

Hao He; Bao Jian Pei; Ho Hsuan Chou; Tian Tian; Wing Hong CHAN; Albert W M LEE

doi:10.1021/ol8005826

Camphor sulfonyl hydrazines (CaSH) as organocatalysts in enantioselective Diels-Alder reactions

Hao He, Bao Jian Pei, Ho Hsuan Chou, Tian Tian, Wing Hong CHAN, Albert W M LEE

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

64 Citations (Scopus)

Abstract

(Chemical Equation Presented) Cyclic sulfonyl hydrazine was demonstrated for the first time as a new functionality for organocatalysis. A series of six-membered cyclic hydrazines derived from camphor sulfonic acid were synthesized. With trichloroacetic acid as cocatalyst, they are efficient organocatalysts for enantioselective Diels-Alder reactions with good chemical yields and up to 96% ee. The reactions took place in brine at 0 °C to room temperature.

Original language	English
Pages (from-to)	2421-2424
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	12
DOIs	https://doi.org/10.1021/ol8005826
Publication status	Published - 2008

Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol8005826

Cite this

@article{94da6b2eb6f74801b3eaf10aa589217b,

title = "Camphor sulfonyl hydrazines (CaSH) as organocatalysts in enantioselective Diels-Alder reactions",

abstract = "(Chemical Equation Presented) Cyclic sulfonyl hydrazine was demonstrated for the first time as a new functionality for organocatalysis. A series of six-membered cyclic hydrazines derived from camphor sulfonic acid were synthesized. With trichloroacetic acid as cocatalyst, they are efficient organocatalysts for enantioselective Diels-Alder reactions with good chemical yields and up to 96% ee. The reactions took place in brine at 0 °C to room temperature.",

author = "Hao He and Pei, {Bao Jian} and Chou, {Ho Hsuan} and Tian Tian and CHAN, {Wing Hong} and LEE, {Albert W M}",

note = "Financial support from the Faculty Research Grant (FRG/07-08/II04) and the CERG Grant from the University Grant Committee are acknowledged. ",

year = "2008",

doi = "10.1021/ol8005826",

language = "English",

volume = "10",

pages = "2421--2424",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "12",

}

TY - JOUR

T1 - Camphor sulfonyl hydrazines (CaSH) as organocatalysts in enantioselective Diels-Alder reactions

AU - He, Hao

AU - Pei, Bao Jian

AU - Chou, Ho Hsuan

AU - Tian, Tian

AU - CHAN, Wing Hong

AU - LEE, Albert W M

N1 - Financial support from the Faculty Research Grant (FRG/07-08/II04) and the CERG Grant from the University Grant Committee are acknowledged.

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) Cyclic sulfonyl hydrazine was demonstrated for the first time as a new functionality for organocatalysis. A series of six-membered cyclic hydrazines derived from camphor sulfonic acid were synthesized. With trichloroacetic acid as cocatalyst, they are efficient organocatalysts for enantioselective Diels-Alder reactions with good chemical yields and up to 96% ee. The reactions took place in brine at 0 °C to room temperature.

AB - (Chemical Equation Presented) Cyclic sulfonyl hydrazine was demonstrated for the first time as a new functionality for organocatalysis. A series of six-membered cyclic hydrazines derived from camphor sulfonic acid were synthesized. With trichloroacetic acid as cocatalyst, they are efficient organocatalysts for enantioselective Diels-Alder reactions with good chemical yields and up to 96% ee. The reactions took place in brine at 0 °C to room temperature.

UR - http://www.scopus.com/inward/record.url?scp=48849100725&partnerID=8YFLogxK

U2 - 10.1021/ol8005826

DO - 10.1021/ol8005826

M3 - Journal article

C2 - 18481866

AN - SCOPUS:48849100725

SN - 1523-7060

VL - 10

SP - 2421

EP - 2424

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Camphor sulfonyl hydrazines (CaSH) as organocatalysts in enantioselective Diels-Alder reactions

Abstract

Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this