Novel Amide-Directed Hydrocarbonylation and Double Carbonylation of N-Allylamides

Iwao Ojima; Zhaoda Zhang

doi:10.1021/jo00253a051

Novel Amide-Directed Hydrocarbonylation and Double Carbonylation of N-Allylamides

Iwao Ojima
, Zhaoda Zhang

Chemistry

Stony Brook University

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

39 Scopus citations

Abstract

The rhodium-catalyzed hydroformylation and palladium-catalyzed hydroesterification of N-allylamides give isoaldehyde (1) and isoester (5), respectively, with good regioselectivity through chelation control while the rhodium- and Co₂Rh₂(CO)₁₂-catalyzed reactions of an Nmethallylamide give a novel double carbonylation product (10) and a pyrrolidine (11), respectively, with excellent selectivity.

Original language	English
Pages (from-to)	4422-4425
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	53
Issue number	18
DOIs	https://doi.org/10.1021/jo00253a051
State	Published - Sep 1 1988

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title = "Novel Amide-Directed Hydrocarbonylation and Double Carbonylation of N-Allylamides",

abstract = "The rhodium-catalyzed hydroformylation and palladium-catalyzed hydroesterification of N-allylamides give isoaldehyde (1) and isoester (5), respectively, with good regioselectivity through chelation control while the rhodium- and Co2Rh2(CO)12-catalyzed reactions of an Nmethallylamide give a novel double carbonylation product (10) and a pyrrolidine (11), respectively, with excellent selectivity.",

author = "Iwao Ojima and Zhaoda Zhang",

year = "1988",

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AU - Ojima, Iwao

AU - Zhang, Zhaoda

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N2 - The rhodium-catalyzed hydroformylation and palladium-catalyzed hydroesterification of N-allylamides give isoaldehyde (1) and isoester (5), respectively, with good regioselectivity through chelation control while the rhodium- and Co2Rh2(CO)12-catalyzed reactions of an Nmethallylamide give a novel double carbonylation product (10) and a pyrrolidine (11), respectively, with excellent selectivity.

AB - The rhodium-catalyzed hydroformylation and palladium-catalyzed hydroesterification of N-allylamides give isoaldehyde (1) and isoester (5), respectively, with good regioselectivity through chelation control while the rhodium- and Co2Rh2(CO)12-catalyzed reactions of an Nmethallylamide give a novel double carbonylation product (10) and a pyrrolidine (11), respectively, with excellent selectivity.

UR - https://www.scopus.com/pages/publications/0000738468

U2 - 10.1021/jo00253a051

DO - 10.1021/jo00253a051

M3 - Article

AN - SCOPUS:0000738468

SN - 0022-3263

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SP - 4422

EP - 4425

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 18

ER -

Novel Amide-Directed Hydrocarbonylation and Double Carbonylation of N-Allylamides

Abstract

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