Organocatalytic synthesis of N-phenylisoxazolidin-5-ones and a one-pot synthesis of β-amino acid esters

Jayasree Seayad; Pranab Kumar Patra; Yugen Zhang; Jackie Y. Ying

doi:10.1021/ol800003n

Organocatalytic synthesis of N-phenylisoxazolidin-5-ones and a one-pot synthesis of β-amino acid esters

Jayasree Seayad
, Pranab Kumar Patra
, Yugen Zhang^*
, Jackie Y. Ying

^*Corresponding author for this work

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

101 Scopus citations

Abstract

A novel N-heterocyclic carbene (NHC)-catalyzed C-N bond formation by the reaction of α,β-unsaturated aldehydes and nitrosobenzene to N-phenylisoxazolidin-5-ones, followed by an acid-catalyzed esterification and Bamberger-like rearrangement in a mild one-pot protocol leads to N-p-methoxyphenyl (N-PMP) protected β-amino acid esters.

Original language	English
Pages (from-to)	953-956
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	5
DOIs	https://doi.org/10.1021/ol800003n
State	Published - 6 Mar 2008
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol800003n

Cite this

@article{f3962b156dc84b8cba78945405e9c928,

title = "Organocatalytic synthesis of N-phenylisoxazolidin-5-ones and a one-pot synthesis of β-amino acid esters",

abstract = "A novel N-heterocyclic carbene (NHC)-catalyzed C-N bond formation by the reaction of α,β-unsaturated aldehydes and nitrosobenzene to N-phenylisoxazolidin-5-ones, followed by an acid-catalyzed esterification and Bamberger-like rearrangement in a mild one-pot protocol leads to N-p-methoxyphenyl (N-PMP) protected β-amino acid esters.",

author = "Jayasree Seayad and Patra, \{Pranab Kumar\} and Yugen Zhang and Ying, \{Jackie Y.\}",

year = "2008",

month = mar,

day = "6",

doi = "10.1021/ol800003n",

language = "English",

volume = "10",

pages = "953--956",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

T1 - Organocatalytic synthesis of N-phenylisoxazolidin-5-ones and a one-pot synthesis of β-amino acid esters

AU - Seayad, Jayasree

AU - Patra, Pranab Kumar

AU - Zhang, Yugen

AU - Ying, Jackie Y.

PY - 2008/3/6

Y1 - 2008/3/6

N2 - A novel N-heterocyclic carbene (NHC)-catalyzed C-N bond formation by the reaction of α,β-unsaturated aldehydes and nitrosobenzene to N-phenylisoxazolidin-5-ones, followed by an acid-catalyzed esterification and Bamberger-like rearrangement in a mild one-pot protocol leads to N-p-methoxyphenyl (N-PMP) protected β-amino acid esters.

AB - A novel N-heterocyclic carbene (NHC)-catalyzed C-N bond formation by the reaction of α,β-unsaturated aldehydes and nitrosobenzene to N-phenylisoxazolidin-5-ones, followed by an acid-catalyzed esterification and Bamberger-like rearrangement in a mild one-pot protocol leads to N-p-methoxyphenyl (N-PMP) protected β-amino acid esters.

UR - https://www.scopus.com/pages/publications/43049137882

U2 - 10.1021/ol800003n

DO - 10.1021/ol800003n

M3 - Article

C2 - 18247633

AN - SCOPUS:43049137882

SN - 1523-7060

VL - 10

SP - 953

EP - 956

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Organocatalytic synthesis of N-phenylisoxazolidin-5-ones and a one-pot synthesis of β-amino acid esters

Abstract

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this