Double allylation reactions of (2-azaallyl)stannanes: synthesis of N,N-bis(3-butenyl)amines and their conversion to 2,3,6,7-tetrahydroazepines via ring-closing metathesis.

doi:10.1021/OL015711W

Paper

Double allylation reactions of (2-azaallyl)stannanes: synthesis of N,N-bis(3-butenyl)amines and their conversion to 2,3,6,7-tetrahydroazepines via ring-closing metathesis.

Published Apr 3, 2001 · W. Pearson, A. Aponick

Organic letters

Q1 SJR score

11

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

[reaction in text] Treatment of (2-azaallyl)stannanes (i) with 2.2 equiv of allylmagnesium bromide afforded good yields of N,N-bis(3-butenyl)amines derivatives (ii), which were subjected to ring-closing metathesis to afford 2,3,6,7-tetrahydroazepines (iii). Thus, (2-azaallyl)stannanes are the synthetic equivalents of amine alpha,alpha'-dications.

Study Snapshot

(2-azaallyl)stannanes can be used to synthesize N,N-bis(3-butenyl)amines and their conversion to 2,3,6,7-tetrahydroazepines via ring-closing metathesis.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

Double allylation reactions of (2-azaallyl)stannanes: synthesis of N,N-bis(3-butenyl)amines and their conversion to 2,3,6,7-tetrahydroazepines via ring-closing metathesis.

Sign up to use Study Snapshot

References

Citations

2-Azaallyl Anions, 2-Azaallyl Cations, 2-Azaallyl Radicals, and Azomethine Ylides.

2-azaallyl anions and cations have become key intermediates in organic synthesis, with recent advances in transition-metal-catalyzed and transition-metal-free transformations.

Olefin Ring‐Closing Metathesis

The olefin ring-closing metathesis reaction catalyzed by ruthenium and molybdenum complexes has revolutionized the synthesis of natural products and drug discovery targets.

Asymmetric synthesis of α-alkenyl homoallylic primary amines via 1,2-addition of Grignard reagent to α,β-unsaturated phosphonyl imines.

Asymmetric synthesis of -alkenyl homoallylic primary amines using 1,2-addition of Grignard reagent to chiral phosphonyl imines yields good yields and excellent diastereoselectivity, making them easily removed.

Synthesis of diarylazepan-4-ones

The study successfully synthesized 3,3-diarylazepan-4-ones and 5,5-diarylazepan-4-ones from commercially available piperidine-3-carboxylic acid ethyl ester and piperidine-4-carboxylic acid ethyl

Azomethine ylides from tin-substituted cyclic carbinol amides: a new route to highly substituted pyrrolizidines.

This novel route to azomethine ylides allows rapid access to highly functionalized pyrrolizidines (1,2,3,9b-tetrahydropyrrolo[2,1-a]isoindol-5-ones).

Functions Incorporating a Nitrogen and a Silicon, Germanium, Boron, or a Metal

Functional groups containing a nitrogen and a metal/semimetal on the same carbon atom are interesting and useful synthetic targets, offering potential for diverse intermediates and structures in organic chemistry.