First synthesis of optically pure propargylic N-hydroxylamines by direct, highly diastereoselective addition of terminal alkynes to nitrones

Roger Fässler; Doug E. Frantz; Jürg Oetiker; Erick M. Carreira

doi:10.1002/1521-3773(20020816)41:16<3054::AID-ANIE3054>3.0.CO;2-B

First synthesis of optically pure propargylic N-hydroxylamines by direct, highly diastereoselective addition of terminal alkynes to nitrones

Roger Fässler
, Doug E. Frantz
, Jürg Oetiker
, Erick M. Carreira

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

134 Scopus citations

Abstract

In situ generation of nucleophilic alkynilides by using substoichiometric amounts of Zn(OTf)₂ (OTf = trifluoromethanesulfonate) followed by removal of the chiral auxiliary enables the direct use of a wide range of terminal acetylenes in the synthesis of optically pure propargylic N-hydroxylamines (see scheme).

Original language	English
Pages (from-to)	3054-3056
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	41
Issue number	16
DOIs	https://doi.org/10.1002/1521-3773(20020816)41:16<3054::AID-ANIE3054>3.0.CO;2-B
State	Published - Aug 16 2002

Keywords

Acetylides
Diastereoselectivity
Glycosylnitrones
Hydroxylamines
Zinc

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10.1002/1521-3773(20020816)41:16<3054::AID-ANIE3054>3.0.CO;2-B

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title = "First synthesis of optically pure propargylic N-hydroxylamines by direct, highly diastereoselective addition of terminal alkynes to nitrones",

abstract = "In situ generation of nucleophilic alkynilides by using substoichiometric amounts of Zn(OTf)2 (OTf = trifluoromethanesulfonate) followed by removal of the chiral auxiliary enables the direct use of a wide range of terminal acetylenes in the synthesis of optically pure propargylic N-hydroxylamines (see scheme).",

keywords = "Acetylides, Diastereoselectivity, Glycosylnitrones, Hydroxylamines, Zinc",

author = "Roger F{\"a}ssler and Frantz, \{Doug E.\} and J{\"u}rg Oetiker and Carreira, \{Erick M.\}",

year = "2002",

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doi = "10.1002/1521-3773(20020816)41:16<3054::AID-ANIE3054>3.0.CO;2-B",

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journal = "Angewandte Chemie - International Edition",

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T1 - First synthesis of optically pure propargylic N-hydroxylamines by direct, highly diastereoselective addition of terminal alkynes to nitrones

AU - Fässler, Roger

AU - Frantz, Doug E.

AU - Oetiker, Jürg

AU - Carreira, Erick M.

PY - 2002/8/16

Y1 - 2002/8/16

N2 - In situ generation of nucleophilic alkynilides by using substoichiometric amounts of Zn(OTf)2 (OTf = trifluoromethanesulfonate) followed by removal of the chiral auxiliary enables the direct use of a wide range of terminal acetylenes in the synthesis of optically pure propargylic N-hydroxylamines (see scheme).

AB - In situ generation of nucleophilic alkynilides by using substoichiometric amounts of Zn(OTf)2 (OTf = trifluoromethanesulfonate) followed by removal of the chiral auxiliary enables the direct use of a wide range of terminal acetylenes in the synthesis of optically pure propargylic N-hydroxylamines (see scheme).

KW - Acetylides

KW - Diastereoselectivity

KW - Glycosylnitrones

KW - Hydroxylamines

KW - Zinc

UR - https://www.scopus.com/pages/publications/0037119338

U2 - 10.1002/1521-3773(20020816)41:16<3054::AID-ANIE3054>3.0.CO;2-B

DO - 10.1002/1521-3773(20020816)41:16<3054::AID-ANIE3054>3.0.CO;2-B

M3 - Article

C2 - 12203456

AN - SCOPUS:0037119338

SN - 1433-7851

VL - 41

SP - 3054

EP - 3056

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 16

ER -

First synthesis of optically pure propargylic N-hydroxylamines by direct, highly diastereoselective addition of terminal alkynes to nitrones

Abstract

Keywords

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