Asymmetric synthesis of diamine derivatives via sequential palladium and rhodium catalysis

Barry M. Trost, Sushant Malhotra, David Olson, Autumn Maruniak, J. Du Bois

Research output: Contribution to journalArticle

66 Citations (Scopus)

Abstract

The use of a bifunctional nitrogen nucleophile and an allyl carbonate starting material in successive enantioselective palladium- and diastereoselective rhodium-catalyzed reactions enables the rapid assembly of unique amino aziridine products. Further elaboration of these materials affords complex, stereodefined polyamine architectures, thus demonstrating the power of these combined methods for simplifying asymmetric C-N bond construction.

Original languageEnglish (US)
Pages (from-to)4190-4191
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number12
DOIs
StatePublished - Apr 1 2009
Externally publishedYes

Fingerprint

Rhodium
Diamines
Carbonates
Polyamines
Palladium
Catalysis
Nitrogen
Derivatives
Nucleophiles
aziridine

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Asymmetric synthesis of diamine derivatives via sequential palladium and rhodium catalysis. / Trost, Barry M.; Malhotra, Sushant; Olson, David; Maruniak, Autumn; Du Bois, J.

In: Journal of the American Chemical Society, Vol. 131, No. 12, 01.04.2009, p. 4190-4191.

Research output: Contribution to journalArticle

Trost, Barry M. ; Malhotra, Sushant ; Olson, David ; Maruniak, Autumn ; Du Bois, J. / Asymmetric synthesis of diamine derivatives via sequential palladium and rhodium catalysis. In: Journal of the American Chemical Society. 2009 ; Vol. 131, No. 12. pp. 4190-4191.
@article{8826115ab0724e82902e39e11743a49e,
title = "Asymmetric synthesis of diamine derivatives via sequential palladium and rhodium catalysis",
abstract = "The use of a bifunctional nitrogen nucleophile and an allyl carbonate starting material in successive enantioselective palladium- and diastereoselective rhodium-catalyzed reactions enables the rapid assembly of unique amino aziridine products. Further elaboration of these materials affords complex, stereodefined polyamine architectures, thus demonstrating the power of these combined methods for simplifying asymmetric C-N bond construction.",
author = "Trost, {Barry M.} and Sushant Malhotra and David Olson and Autumn Maruniak and {Du Bois}, J.",
year = "2009",
month = "4",
day = "1",
doi = "10.1021/ja809697p",
language = "English (US)",
volume = "131",
pages = "4190--4191",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "12",

}

TY - JOUR

T1 - Asymmetric synthesis of diamine derivatives via sequential palladium and rhodium catalysis

AU - Trost, Barry M.

AU - Malhotra, Sushant

AU - Olson, David

AU - Maruniak, Autumn

AU - Du Bois, J.

PY - 2009/4/1

Y1 - 2009/4/1

N2 - The use of a bifunctional nitrogen nucleophile and an allyl carbonate starting material in successive enantioselective palladium- and diastereoselective rhodium-catalyzed reactions enables the rapid assembly of unique amino aziridine products. Further elaboration of these materials affords complex, stereodefined polyamine architectures, thus demonstrating the power of these combined methods for simplifying asymmetric C-N bond construction.

AB - The use of a bifunctional nitrogen nucleophile and an allyl carbonate starting material in successive enantioselective palladium- and diastereoselective rhodium-catalyzed reactions enables the rapid assembly of unique amino aziridine products. Further elaboration of these materials affords complex, stereodefined polyamine architectures, thus demonstrating the power of these combined methods for simplifying asymmetric C-N bond construction.

UR - http://www.scopus.com/inward/record.url?scp=67849128913&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=67849128913&partnerID=8YFLogxK

U2 - 10.1021/ja809697p

DO - 10.1021/ja809697p

M3 - Article

C2 - 19275160

AN - SCOPUS:67849128913

VL - 131

SP - 4190

EP - 4191

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 12

ER -