Asymmetric brønsted acid catalyzed nucleophilic addition to in situ generated chiral N-acyliminium ions

Magnus Rueping; Boris J. Nachtsheim

doi:10.1055/s-0029-1218539

Asymmetric brønsted acid catalyzed nucleophilic addition to in situ generated chiral N-acyliminium ions

Magnus Rueping^*, Boris J. Nachtsheim

^*Corresponding author for this work

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

92 Scopus citations

Abstract

A new enantioselective Brønsted acid catalyzed nucleophilic substitution of γ-hydroxylactams with indole is presented. The reaction proceeds via an intermediary N-acyliminium ion and provides disubstituted γ-lactams in good yields and with high enantioselectivities.

Original language	English (US)
Pages (from-to)	119-122
Number of pages	4
Journal	Synlett
Issue number	1
DOIs	https://doi.org/10.1055/s-0029-1218539
State	Published - 2010
Externally published	Yes

Keywords

Amino acid
Nucleophilic substitution
Organocatalysis
Protonation
Quaternary stereocenter

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1055/s-0029-1218539

Cite this

@article{446522366d0b46daa57767e2c6a89ba6,

title = "Asymmetric br{\o}nsted acid catalyzed nucleophilic addition to in situ generated chiral N-acyliminium ions",

abstract = "A new enantioselective Br{\o}nsted acid catalyzed nucleophilic substitution of γ-hydroxylactams with indole is presented. The reaction proceeds via an intermediary N-acyliminium ion and provides disubstituted γ-lactams in good yields and with high enantioselectivities.",

keywords = "Amino acid, Nucleophilic substitution, Organocatalysis, Protonation, Quaternary stereocenter",

author = "Magnus Rueping and Nachtsheim, {Boris J.}",

year = "2010",

doi = "10.1055/s-0029-1218539",

language = "English (US)",

pages = "119--122",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "1",

}

TY - JOUR

T1 - Asymmetric brønsted acid catalyzed nucleophilic addition to in situ generated chiral N-acyliminium ions

AU - Rueping, Magnus

AU - Nachtsheim, Boris J.

PY - 2010

Y1 - 2010

N2 - A new enantioselective Brønsted acid catalyzed nucleophilic substitution of γ-hydroxylactams with indole is presented. The reaction proceeds via an intermediary N-acyliminium ion and provides disubstituted γ-lactams in good yields and with high enantioselectivities.

AB - A new enantioselective Brønsted acid catalyzed nucleophilic substitution of γ-hydroxylactams with indole is presented. The reaction proceeds via an intermediary N-acyliminium ion and provides disubstituted γ-lactams in good yields and with high enantioselectivities.

KW - Amino acid

KW - Nucleophilic substitution

KW - Organocatalysis

KW - Protonation

KW - Quaternary stereocenter

UR - http://www.scopus.com/inward/record.url?scp=77949904394&partnerID=8YFLogxK

U2 - 10.1055/s-0029-1218539

DO - 10.1055/s-0029-1218539

M3 - Article

AN - SCOPUS:77949904394

SN - 0936-5214

SP - 119

EP - 122

JO - Synlett

JF - Synlett

IS - 1

ER -

Asymmetric brønsted acid catalyzed nucleophilic addition to in situ generated chiral N-acyliminium ions

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this