Osmium-catalyzed olefin dihydroxylation and aminohydroxylation in the second catalytic cycle

Peng Wu, Robert Hilgraf, Valery V. Fokin

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Two catalytic cycles operate in the osmium-catalyzed olefin dihydroxylation and aminohydroxylation. Slow hydrolysis of the Os(VI) monoglycolate (or monoazaglycolate in aminohydroxylation) intermediate often results in the addition of another molecule of olefin thereby shunting the catalysis into the second catalytic cycle. As a result, both enantio- and chemoselectivity are reduced. A series of new chelating ligands were devised, which force the catalysis into the second cycle while maintaining enantiocontrol in the olefin addition step. Excellent catalytic turnover and moderate to good enantioselectivity were achieved.

Original languageEnglish (US)
Pages (from-to)1079-1085
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume348
Issue number9
DOIs
StatePublished - Jun 2006
Externally publishedYes

Fingerprint

Osmium
Alkenes
Olefins
Enantioselectivity
Catalysis
Chelation
Hydrolysis
Ligands
Molecules

Keywords

  • Alkenes
  • Aminohydroxylations
  • Asymmetric catalysis
  • Dihydroxylations
  • Osmium

ASJC Scopus subject areas

  • Chemistry (miscellaneous)
  • Organic Chemistry
  • Catalysis

Cite this

Osmium-catalyzed olefin dihydroxylation and aminohydroxylation in the second catalytic cycle. / Wu, Peng; Hilgraf, Robert; Fokin, Valery V.

In: Advanced Synthesis and Catalysis, Vol. 348, No. 9, 06.2006, p. 1079-1085.

Research output: Contribution to journalArticle

Wu, Peng ; Hilgraf, Robert ; Fokin, Valery V. / Osmium-catalyzed olefin dihydroxylation and aminohydroxylation in the second catalytic cycle. In: Advanced Synthesis and Catalysis. 2006 ; Vol. 348, No. 9. pp. 1079-1085.
@article{587307d5d812459fa38b1506713f5717,
title = "Osmium-catalyzed olefin dihydroxylation and aminohydroxylation in the second catalytic cycle",
abstract = "Two catalytic cycles operate in the osmium-catalyzed olefin dihydroxylation and aminohydroxylation. Slow hydrolysis of the Os(VI) monoglycolate (or monoazaglycolate in aminohydroxylation) intermediate often results in the addition of another molecule of olefin thereby shunting the catalysis into the second catalytic cycle. As a result, both enantio- and chemoselectivity are reduced. A series of new chelating ligands were devised, which force the catalysis into the second cycle while maintaining enantiocontrol in the olefin addition step. Excellent catalytic turnover and moderate to good enantioselectivity were achieved.",
keywords = "Alkenes, Aminohydroxylations, Asymmetric catalysis, Dihydroxylations, Osmium",
author = "Peng Wu and Robert Hilgraf and Fokin, {Valery V.}",
year = "2006",
month = "6",
doi = "10.1002/adsc.200505252",
language = "English (US)",
volume = "348",
pages = "1079--1085",
journal = "Advanced Synthesis and Catalysis",
issn = "1615-4150",
publisher = "Wiley-VCH Verlag",
number = "9",

}

TY - JOUR

T1 - Osmium-catalyzed olefin dihydroxylation and aminohydroxylation in the second catalytic cycle

AU - Wu, Peng

AU - Hilgraf, Robert

AU - Fokin, Valery V.

PY - 2006/6

Y1 - 2006/6

N2 - Two catalytic cycles operate in the osmium-catalyzed olefin dihydroxylation and aminohydroxylation. Slow hydrolysis of the Os(VI) monoglycolate (or monoazaglycolate in aminohydroxylation) intermediate often results in the addition of another molecule of olefin thereby shunting the catalysis into the second catalytic cycle. As a result, both enantio- and chemoselectivity are reduced. A series of new chelating ligands were devised, which force the catalysis into the second cycle while maintaining enantiocontrol in the olefin addition step. Excellent catalytic turnover and moderate to good enantioselectivity were achieved.

AB - Two catalytic cycles operate in the osmium-catalyzed olefin dihydroxylation and aminohydroxylation. Slow hydrolysis of the Os(VI) monoglycolate (or monoazaglycolate in aminohydroxylation) intermediate often results in the addition of another molecule of olefin thereby shunting the catalysis into the second catalytic cycle. As a result, both enantio- and chemoselectivity are reduced. A series of new chelating ligands were devised, which force the catalysis into the second cycle while maintaining enantiocontrol in the olefin addition step. Excellent catalytic turnover and moderate to good enantioselectivity were achieved.

KW - Alkenes

KW - Aminohydroxylations

KW - Asymmetric catalysis

KW - Dihydroxylations

KW - Osmium

UR - http://www.scopus.com/inward/record.url?scp=33745725889&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33745725889&partnerID=8YFLogxK

U2 - 10.1002/adsc.200505252

DO - 10.1002/adsc.200505252

M3 - Article

AN - SCOPUS:33745725889

VL - 348

SP - 1079

EP - 1085

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

IS - 9

ER -