Deuterium as a stereochemically invisible blocking group for chiral ligand synthesis

Ross A. Arthurs; Christopher J. Richards

doi:10.1021/acs.orglett.6b03874

Deuterium as a stereochemically invisible blocking group for chiral ligand synthesis

Ross A. Arthurs, Christopher J. Richards

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

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Abstract

Highly diastereoselective lithiation (s-BuLi/TMEDA ix Et2O, -78 degrees C, 2 h) of (5)-2-ferroceny1-4-(substituted)-oxazolines followed by addition of MeOH-d(4) gave up to 95% D incorporation. Subsequent application of alternative lithiation conditions (n-BuLi in THF, -78 degrees C, 2 h), followed by addition of an electrophile, resulted in a reversal of diastereoselectivity controlled primarily by the high k(H)/k(D) value for lithiation (isomer ratio typically between 10:1 and 20:1).

Original language	English
Pages (from-to)	702-705
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	3
Early online date	24 Jan 2017
DOIs	https://doi.org/10.1021/acs.orglett.6b03874
Publication status	Published - 3 Feb 2017

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10.1021/acs.orglett.6b03874

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Chris Richards
- Chris.Richardsuea.acuk
- School of Chemistry, Pharmacy and Pharmacology - Reader in Organic Chemistry
- Chemistry of Materials and Catalysis - Member
Person: Research Group Member, Academic, Teaching & Research

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title = "Deuterium as a stereochemically invisible blocking group for chiral ligand synthesis",

abstract = "Highly diastereoselective lithiation (s-BuLi/TMEDA ix Et2O, -78 degrees C, 2 h) of (5)-2-ferroceny1-4-(substituted)-oxazolines followed by addition of MeOH-d(4) gave up to 95% D incorporation. Subsequent application of alternative lithiation conditions (n-BuLi in THF, -78 degrees C, 2 h), followed by addition of an electrophile, resulted in a reversal of diastereoselectivity controlled primarily by the high k(H)/k(D) value for lithiation (isomer ratio typically between 10:1 and 20:1).",

author = "Arthurs, {Ross A.} and Richards, {Christopher J.}",

year = "2017",

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doi = "10.1021/acs.orglett.6b03874",

language = "English",

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AU - Arthurs, Ross A.

AU - Richards, Christopher J.

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Y1 - 2017/2/3

N2 - Highly diastereoselective lithiation (s-BuLi/TMEDA ix Et2O, -78 degrees C, 2 h) of (5)-2-ferroceny1-4-(substituted)-oxazolines followed by addition of MeOH-d(4) gave up to 95% D incorporation. Subsequent application of alternative lithiation conditions (n-BuLi in THF, -78 degrees C, 2 h), followed by addition of an electrophile, resulted in a reversal of diastereoselectivity controlled primarily by the high k(H)/k(D) value for lithiation (isomer ratio typically between 10:1 and 20:1).

AB - Highly diastereoselective lithiation (s-BuLi/TMEDA ix Et2O, -78 degrees C, 2 h) of (5)-2-ferroceny1-4-(substituted)-oxazolines followed by addition of MeOH-d(4) gave up to 95% D incorporation. Subsequent application of alternative lithiation conditions (n-BuLi in THF, -78 degrees C, 2 h), followed by addition of an electrophile, resulted in a reversal of diastereoselectivity controlled primarily by the high k(H)/k(D) value for lithiation (isomer ratio typically between 10:1 and 20:1).

U2 - 10.1021/acs.orglett.6b03874

DO - 10.1021/acs.orglett.6b03874

M3 - Article

VL - 19

SP - 702

EP - 705

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 3

ER -

Deuterium as a stereochemically invisible blocking group for chiral ligand synthesis

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