A Protocol for the exo-Mono and exo,exo-Bis Functionalization of the Diazocine Ring of Tröger's Base.

Sami Dawaigher; Kristoffer Månsson; Erhad Ascic; Josep Artacho Ruiz; Roger Mårtensson; Nagarajan Loganathan; Ola Wendt; Michael Harmata; Victor Snieckus; Kenneth Wärnmark

doi:10.1021/acs.joc.5b01921

A Protocol for the exo-Mono and exo,exo-Bis Functionalization of the Diazocine Ring of Tröger's Base.

Sami Dawaigher, Kristoffer Månsson, Erhad Ascic, Josep Artacho Ruiz, Roger Mårtensson, Nagarajan Loganathan, Ola Wendt, Michael Harmata, Victor Snieckus, Kenneth Wärnmark

Centre for Analysis and Synthesis

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

Abstract

An efficient protocol has been developed for the exo-mono and exo,exo-bis functionalization of Tröger's base in the benzylic 6 and 12 positions of the diazocine ring. The lithiation of Tröger's base using s-BuLi/TMEDA followed by electrophilic quench affords exo-mono- and exo,exo-bis-substituted derivatives of Tröger's base in good to excellent yields. The variation of the number of equivalents of s-BuLi/TMEDA and the order of addition of the electrophile strongly govern the outcome of the reaction for each electrophile.

Original language	English
Pages (from-to)	12006-12014
Journal	Journal of Organic Chemistry
Volume	80
Issue number	24
DOIs	https://doi.org/10.1021/acs.joc.5b01921
Publication status	Published - 2015

Subject classification (UKÄ)

Organic Chemistry

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10.1021/acs.joc.5b01921

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title = "A Protocol for the exo-Mono and exo,exo-Bis Functionalization of the Diazocine Ring of Tr{\"o}ger's Base.",

abstract = "An efficient protocol has been developed for the exo-mono and exo,exo-bis functionalization of Tr{\"o}ger's base in the benzylic 6 and 12 positions of the diazocine ring. The lithiation of Tr{\"o}ger's base using s-BuLi/TMEDA followed by electrophilic quench affords exo-mono- and exo,exo-bis-substituted derivatives of Tr{\"o}ger's base in good to excellent yields. The variation of the number of equivalents of s-BuLi/TMEDA and the order of addition of the electrophile strongly govern the outcome of the reaction for each electrophile.",

author = "Sami Dawaigher and Kristoffer M{\aa}nsson and Erhad Ascic and {Artacho Ruiz}, Josep and Roger M{\aa}rtensson and Nagarajan Loganathan and Ola Wendt and Michael Harmata and Victor Snieckus and Kenneth W{\"a}rnmark",

year = "2015",

doi = "10.1021/acs.joc.5b01921",

language = "English",

volume = "80",

pages = "12006--12014",

journal = "Journal of Organic Chemistry",

issn = "1520-6904",

publisher = "The American Chemical Society (ACS)",

number = "24",

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TY - JOUR

T1 - A Protocol for the exo-Mono and exo,exo-Bis Functionalization of the Diazocine Ring of Tröger's Base.

AU - Dawaigher, Sami

AU - Månsson, Kristoffer

AU - Ascic, Erhad

AU - Artacho Ruiz, Josep

AU - Mårtensson, Roger

AU - Loganathan, Nagarajan

AU - Wendt, Ola

AU - Harmata, Michael

AU - Snieckus, Victor

AU - Wärnmark, Kenneth

PY - 2015

Y1 - 2015

N2 - An efficient protocol has been developed for the exo-mono and exo,exo-bis functionalization of Tröger's base in the benzylic 6 and 12 positions of the diazocine ring. The lithiation of Tröger's base using s-BuLi/TMEDA followed by electrophilic quench affords exo-mono- and exo,exo-bis-substituted derivatives of Tröger's base in good to excellent yields. The variation of the number of equivalents of s-BuLi/TMEDA and the order of addition of the electrophile strongly govern the outcome of the reaction for each electrophile.

AB - An efficient protocol has been developed for the exo-mono and exo,exo-bis functionalization of Tröger's base in the benzylic 6 and 12 positions of the diazocine ring. The lithiation of Tröger's base using s-BuLi/TMEDA followed by electrophilic quench affords exo-mono- and exo,exo-bis-substituted derivatives of Tröger's base in good to excellent yields. The variation of the number of equivalents of s-BuLi/TMEDA and the order of addition of the electrophile strongly govern the outcome of the reaction for each electrophile.

U2 - 10.1021/acs.joc.5b01921

DO - 10.1021/acs.joc.5b01921

M3 - Article

C2 - 26597045

SN - 1520-6904

VL - 80

SP - 12006

EP - 12014

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 24

ER -

A Protocol for the exo-Mono and exo,exo-Bis Functionalization of the Diazocine Ring of Tröger's Base.

Abstract

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