In-line proximity effects in extended 7-azanorbornanes.: 1. a new concept for modifying effector group separation based on the control of N-invertomer geometry

Douglas N. Butler; Malcom L.A. Hammond; Martin R. Johnston; Guangxing Sun; John R. Malpass; John Fawcett; Ronald N. Warrener

doi:10.1021/ol9910969

In-line proximity effects in extended 7-azanorbornanes. 1. a new concept for modifying effector group separation based on the control of N-invertomer geometry

Douglas N. Butler, Malcom L.A. Hammond, Martin R. Johnston, Guangxing Sun, John R. Malpass, John Fawcett, Ronald N. Warrener

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

22 Citations (Scopus)

Abstract

(figure presented) X,Y = CH₂ ≈ spirocyclopropyl > C=CMe₂ > NZ > O sentinel dominance control (X>Y) Control of N-substituent geometry in fused 7-azanorbornane systems is based on the dominance of one proximate bridge (sentinel X) over the other (sentinel Y) relative to the N-bridge; the N-inversion equilibrium can effectively be displaced in favor of a single invertomer. This study has used a combination of synthesis, crystallography, and molecular modeling to establish stereostructures.

Original language	English
Pages (from-to)	721-724
Number of pages	4
Journal	Organic Letters
Volume	2
Issue number	6
DOIs	https://doi.org/10.1021/ol9910969
Publication status	Published - 3 Mar 2000
Externally published	Yes

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title = "In-line proximity effects in extended 7-azanorbornanes.: 1. a new concept for modifying effector group separation based on the control of N-invertomer geometry",

abstract = "(figure presented) X,Y = CH2 ≈ spirocyclopropyl > C=CMe2 > NZ > O sentinel dominance control (X>Y) Control of N-substituent geometry in fused 7-azanorbornane systems is based on the dominance of one proximate bridge (sentinel X) over the other (sentinel Y) relative to the N-bridge; the N-inversion equilibrium can effectively be displaced in favor of a single invertomer. This study has used a combination of synthesis, crystallography, and molecular modeling to establish stereostructures.",

author = "Butler, {Douglas N.} and Hammond, {Malcom L.A.} and Johnston, {Martin R.} and Guangxing Sun and Malpass, {John R.} and John Fawcett and Warrener, {Ronald N.}",

year = "2000",

month = mar,

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doi = "10.1021/ol9910969",

language = "English",

volume = "2",

pages = "721--724",

journal = "Organic Letters",

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publisher = "American Chemical Society",

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T1 - In-line proximity effects in extended 7-azanorbornanes.

T2 - 1. a new concept for modifying effector group separation based on the control of N-invertomer geometry

AU - Butler, Douglas N.

AU - Hammond, Malcom L.A.

AU - Johnston, Martin R.

AU - Sun, Guangxing

AU - Malpass, John R.

AU - Fawcett, John

AU - Warrener, Ronald N.

PY - 2000/3/3

Y1 - 2000/3/3

N2 - (figure presented) X,Y = CH2 ≈ spirocyclopropyl > C=CMe2 > NZ > O sentinel dominance control (X>Y) Control of N-substituent geometry in fused 7-azanorbornane systems is based on the dominance of one proximate bridge (sentinel X) over the other (sentinel Y) relative to the N-bridge; the N-inversion equilibrium can effectively be displaced in favor of a single invertomer. This study has used a combination of synthesis, crystallography, and molecular modeling to establish stereostructures.

AB - (figure presented) X,Y = CH2 ≈ spirocyclopropyl > C=CMe2 > NZ > O sentinel dominance control (X>Y) Control of N-substituent geometry in fused 7-azanorbornane systems is based on the dominance of one proximate bridge (sentinel X) over the other (sentinel Y) relative to the N-bridge; the N-inversion equilibrium can effectively be displaced in favor of a single invertomer. This study has used a combination of synthesis, crystallography, and molecular modeling to establish stereostructures.

UR - http://www.scopus.com/inward/record.url?scp=0001178805&partnerID=8YFLogxK

U2 - 10.1021/ol9910969

DO - 10.1021/ol9910969

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AN - SCOPUS:0001178805

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VL - 2

SP - 721

EP - 724

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

In-line proximity effects in extended 7-azanorbornanes. 1. a new concept for modifying effector group separation based on the control of N-invertomer geometry

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