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Literature DB >> 14723554

Rhodium-catalyzed asymmetric 1,6-addition of aryltitanates to enynones giving axially chiral allenes.

Tamio Hayashi¹, Norihito Tokunaga, Kazuya Inoue.

Abstract

[reaction: see text] The addition of aryltitanate reagents ArTi(OPr-i)4Li to 3-alkynyl-2-en-1-ones in the presence of chlorotrimethylsilane and a rhodium-(R)-segphos as a catalyst proceeded in a 1,6-fashion to give a high yield of axially chiral allenylalkenyl silyl enol ethers with up to 93% ee.

Entities: Chemical

Year: 2004 PMID： 14723554 DOI： 10.1021/ol036309f

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

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Cited

10 in total

1. Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design.

Authors: Nathan J Adamson; Haleh Jeddi; Steven J Malcolmson
Journal: J Am Chem Soc Date: 2019-05-15 Impact factor: 15.419

2. Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination.

Authors: Thomas J O'Connor; Binh Khanh Mai; Jordan Nafie; Peng Liu; F Dean Toste
Journal: J Am Chem Soc Date: 2021-08-16 Impact factor: 16.383

3. Phase-transfer-catalysed asymmetric synthesis of tetrasubstituted allenes.

Authors: Takuya Hashimoto; Kazuki Sakata; Fumiko Tamakuni; Mark J Dutton; Keiji Maruoka
Journal: Nat Chem Date: 2013-02-10 Impact factor: 24.427

4. Enantioselective Synthesis of Trisubstituted Allenyl-B(pin) Compounds by Phosphine-Cu-Catalyzed 1,3-Enyne Hydroboration. Insights Regarding Stereochemical Integrity of Cu-Allenyl Intermediates.

Authors: Youming Huang; Juan Del Pozo; Sebastian Torker; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2018-02-08 Impact factor: 15.419

5. Efficient Synthesis of Chiral Trisubstituted 1,2-Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes.

Authors: Qian Yao; Yuting Liao; Lili Lin; Xiaobin Lin; Jie Ji; Xiaohua Liu; Xiaoming Feng
Journal: Angew Chem Int Ed Engl Date: 2015-12-22 Impact factor: 15.336

Rhodium-catalyzed asymmetric 1,6-addition of aryltitanates to enynones giving axially chiral allenes.

1. Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design.

2. Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination.

3. Phase-transfer-catalysed asymmetric synthesis of tetrasubstituted allenes.

4. Enantioselective Synthesis of Trisubstituted Allenyl-B(pin) Compounds by Phosphine-Cu-Catalyzed 1,3-Enyne Hydroboration. Insights Regarding Stereochemical Integrity of Cu-Allenyl Intermediates.

5. Efficient Synthesis of Chiral Trisubstituted 1,2-Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes.

6. Organocatalytic synthesis of chiral tetrasubstituted allenes from racemic propargylic alcohols.

7. Rhodium(I)-Complexes Catalyzed 1,4-Conjugate Addition of Arylzinc Chlorides to N-Boc-4-pyridone.

8. Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes.

9. Enantiodivergent Synthesis of Allenes by Point-to-Axial Chirality Transfer.

10. Ruthenium(ii)-catalyzed regioselective 1,6-conjugate addition of umpolung aldehydes as carbanion equivalents.