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Literature DB >> 35041437

Ring Opening of Epoxides by Pendant Silanols.

Someshwar Nagamalla¹, Joel T Mague², Shyam Sathyamoorthi¹.

Abstract

We present a new ring-opening reaction of epoxides by pendant silanols, catalyzed by either Ph3C+BF4- or BINOL-phosphoric acid. Silanol epoxides derived from trans-allylic alcohols, cis-allylic alcohols, trans-homoallylic alcohols, and cis-homoallylic alcohols were all compatible and gave products from either endo- or exo-ring opening. With silanol epoxides derived from 4-alkenyl silanols, an unusual rearrangement to tetrahydrofuran products was observed. The utility of this methodology was demonstrated in a short preparation of protected d-arabitol.

Entities: Chemical

Year: 2022 PMID： 35041437 PMCID： PMC8965746 DOI： 10.1021/acs.orglett.1c04310

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

11 in total

1. Enantioselective epoxidation of allylic alcohols by a chiral complex of vanadium: an effective controller system and a rational mechanistic model.

Authors: Wei Zhang; Arindrajit Basak; Yuji Kosugi; Yujiro Hoshino; Hisashi Yamamoto
Journal: Angew Chem Int Ed Engl Date: 2005-07-11 Impact factor: 15.336

2. Stereocontrolled Synthesis of Tetrafluoropentanols: Multivicinal Fluorinated Alkane Units for Drug Discovery.

Authors: Patrick Bentler; Nathalie Erdeljac; Kathrin Bussmann; Marie Ahlqvist; Laurent Knerr; Klaus Bergander; Constantin G Daniliuc; Ryan Gilmour
Journal: Org Lett Date: 2019-08-09 Impact factor: 6.005

Review 3. Asymmetric catalysis of epoxide ring-opening reactions.

Authors: E N Jacobsen
Journal: Acc Chem Res Date: 2000-06 Impact factor: 22.384

4. Unusual Rearrangement-Remercuration Reactions of Allylic Silanols.

Authors: Someshwar Nagamalla; Ranjeet A Dhokale; Frederick J Seidl; Joel T Mague; Shyam Sathyamoorthi
Journal: Org Chem Front Date: 2021-08-03 Impact factor: 5.456

5. The C2 selective nucleophilic substitution reactions of 2,3-epoxy alcohols mediated by trialkyl borates: the first endo-mode epoxide-opening reaction through an intramolecular metal chelate.

Authors: Minoru Sasaki; Keiji Tanino; Atsushi Hirai; Masaaki Miyashita
Journal: Org Lett Date: 2003-05-15 Impact factor: 6.005

Ring Opening of Epoxides by Pendant Silanols.

1. Enantioselective epoxidation of allylic alcohols by a chiral complex of vanadium: an effective controller system and a rational mechanistic model.

2. Stereocontrolled Synthesis of Tetrafluoropentanols: Multivicinal Fluorinated Alkane Units for Drug Discovery.

Review 3. Asymmetric catalysis of epoxide ring-opening reactions.

4. Unusual Rearrangement-Remercuration Reactions of Allylic Silanols.

5. The C2 selective nucleophilic substitution reactions of 2,3-epoxy alcohols mediated by trialkyl borates: the first endo-mode epoxide-opening reaction through an intramolecular metal chelate.

6. Borinic Acid-Catalyzed, Regioselective Ring Opening of 3,4-Epoxy Alcohols.

7. Tethered Silanoxyiodination of Alkenes.

8. A Formal Rearrangement of Allylic Silanols.

1. Ring Opening of Epoxides by Pendant Silanols.