Asymmetric synthesis of diamine derivatives via sequential palladium and rhodium catalysis

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

doi:10.1021/ja809697p

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 journal › Article

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 language	English (US)
Pages (from-to)	4190-4191
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	131
Issue number	12
DOIs	https://doi.org/10.1021/ja809697p
State	Published - Apr 1 2009
Externally published	Yes

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

Trost, B. M., Malhotra, S., Olson, D., Maruniak, A., & Du Bois, J. (2009). Asymmetric synthesis of diamine derivatives via sequential palladium and rhodium catalysis. Journal of the American Chemical Society, 131(12), 4190-4191. https://doi.org/10.1021/ja809697p

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 journal › Article

Trost, BM, Malhotra, S, Olson, D, Maruniak, A & Du Bois, J 2009, 'Asymmetric synthesis of diamine derivatives via sequential palladium and rhodium catalysis', Journal of the American Chemical Society, vol. 131, no. 12, pp. 4190-4191. https://doi.org/10.1021/ja809697p

Trost BM, Malhotra S, Olson D, Maruniak A, Du Bois J. Asymmetric synthesis of diamine derivatives via sequential palladium and rhodium catalysis. Journal of the American Chemical Society. 2009 Apr 1;131(12):4190-4191. https://doi.org/10.1021/ja809697p

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 -

Access to Document

10.1021/ja809697p