O-substituted alkyl aldehydes for rhodium-catalyzed intermolecular alkyne hydroacylation: the utility of methylthiomethyl ethers

Scott R. Parsons; Joel F. Hooper; Michael C. Willis

doi:10.1021/ol1030662

O-substituted alkyl aldehydes for rhodium-catalyzed intermolecular alkyne hydroacylation: the utility of methylthiomethyl ethers

Scott R. Parsons, Joel F. Hooper, Michael C. Willis

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

43 Citations (Scopus)

Abstract

Combining α-methylthiomethyl (MTM) ether substituted aldehydes and 1-alkynes in the presence of [Rh(dppe)]ClO 4 results in efficient intermolecular alkyne hydroacylation to deliver α-O-MTM-substituted enone products. The product MTM ethers can be converted to the free hydroxyl group either in situ, by the addition of water to the completed reaction, or in a separate operation, by the action of silver nitrate.

Original language	English
Pages (from-to)	998-1000
Number of pages	3
Journal	Organic Letters
Volume	13
Issue number	5
DOIs	https://doi.org/10.1021/ol1030662
Publication status	Published - 4 Mar 2011
Externally published	Yes

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title = "O-substituted alkyl aldehydes for rhodium-catalyzed intermolecular alkyne hydroacylation: the utility of methylthiomethyl ethers",

abstract = "Combining α-methylthiomethyl (MTM) ether substituted aldehydes and 1-alkynes in the presence of [Rh(dppe)]ClO 4 results in efficient intermolecular alkyne hydroacylation to deliver α-O-MTM-substituted enone products. The product MTM ethers can be converted to the free hydroxyl group either in situ, by the addition of water to the completed reaction, or in a separate operation, by the action of silver nitrate.",

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journal = "Organic Letters",

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T1 - O-substituted alkyl aldehydes for rhodium-catalyzed intermolecular alkyne hydroacylation: the utility of methylthiomethyl ethers

AU - Parsons, Scott R.

AU - Hooper, Joel F.

AU - Willis, Michael C.

PY - 2011/3/4

Y1 - 2011/3/4

N2 - Combining α-methylthiomethyl (MTM) ether substituted aldehydes and 1-alkynes in the presence of [Rh(dppe)]ClO 4 results in efficient intermolecular alkyne hydroacylation to deliver α-O-MTM-substituted enone products. The product MTM ethers can be converted to the free hydroxyl group either in situ, by the addition of water to the completed reaction, or in a separate operation, by the action of silver nitrate.

AB - Combining α-methylthiomethyl (MTM) ether substituted aldehydes and 1-alkynes in the presence of [Rh(dppe)]ClO 4 results in efficient intermolecular alkyne hydroacylation to deliver α-O-MTM-substituted enone products. The product MTM ethers can be converted to the free hydroxyl group either in situ, by the addition of water to the completed reaction, or in a separate operation, by the action of silver nitrate.

UR - http://pubs.acs.org/doi/pdf/10.1021/ol1030662

U2 - 10.1021/ol1030662

DO - 10.1021/ol1030662

M3 - Article

SN - 1523-7060

VL - 13

SP - 998

EP - 1000

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

O-substituted alkyl aldehydes for rhodium-catalyzed intermolecular alkyne hydroacylation: the utility of methylthiomethyl ethers

Abstract

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