Lithium‐Catalyzed Thiol Alkylation with Tertiary and Secondary Alcohols: Synthesis of 3‐Sulfanyl‐Oxetanes as Bioisosteres
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- Rosemary A. Croft
- Department of Chemistry Imperial College London South Kensington, London SW7 2AZ UK
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- James J. Mousseau
- Pfizer Medicine Design Eastern Point Road Groton CT 06340 USA
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- Chulho Choi
- Pfizer Medicine Design Eastern Point Road Groton CT 06340 USA
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- James A. Bull
- Department of Chemistry Imperial College London South Kensington, London SW7 2AZ UK
抄録
<jats:title>Abstract</jats:title><jats:p>3‐Sulfanyl‐oxetanes are presented as promising novel bioisosteric replacements for thioesters or benzyl sulfides. From oxetan‐3‐ols, a mild and inexpensive Li catalyst enables chemoselective C−OH activation and thiol alkylation. Oxetane sulfides are formed from various thiols providing novel motifs in new chemical space and specifically as bioisosteres for thioesters due to their similar shape and electronic properties. Under the same conditions, various π‐activated secondary and tertiary alcohols are also successful. Derivatization of the oxetane sulfide linker provides further novel oxetane classes and building blocks. Comparisons of key physicochemical properties of the oxetane compounds to selected carbonyl and methylene analogues indicate that these motifs are suitable for incorporation into drug discovery efforts.</jats:p>
収録刊行物
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- Chemistry – A European Journal
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Chemistry – A European Journal 24 (4), 818-821, 2017-12-20
Wiley