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Literature DB >> 12047153

Stereoselectivity of the benzannulation reaction: efficient central-to-axial chirality transfer.

Andrei V Vorogushin¹, William D Wulff, Hans-Jürgen Hansen.

Abstract

High diastereoselectivity is observed in the preparation of configurationally stable allocolchicinoids 5 from Fischer carbene complexes 4 and 1-pentyne. The analogous reaction of complexes 8 gives 9 with moderate diastereoselectivity for the opposite atropisomer and this selectivity can be taken to high levels under thermodynamic conditions.

Entities: Chemical

Mesh：

Substances：
allocolchicine
Colchicine

Year: 2002 PMID： 12047153 DOI： 10.1021/ja0201505

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

5 in total

1. Central-to-Axial Chirality Transfer in the Benzannulation Reaction of Optically Pure Fischer Carbene Complexes in the Synthesis of Allocolchicinoids.

Authors: Andrei V Vorogushin; William D Wulff; Hans-Jürgen Hansen
Journal: Tetrahedron Date: 2008-01-28 Impact factor: 2.457

2. Remarkably diastereoselective synthesis of a chiral biphenyl diphosphine ligand and its application in asymmetric hydrogenation.

Authors: Liqin Qiu; Jing Wu; Shusun Chan; Terry T-L Au-Yeung; Jian-Xin Ji; Rongwei Guo; Cheng-Chao Pai; Zhongyuan Zhou; Xingshu Li; Qing-Hua Fan; Albert S C Chan
Journal: Proc Natl Acad Sci U S A Date: 2004-04-05 Impact factor: 11.205

Stereoselectivity of the benzannulation reaction: efficient central-to-axial chirality transfer.

1. Central-to-Axial Chirality Transfer in the Benzannulation Reaction of Optically Pure Fischer Carbene Complexes in the Synthesis of Allocolchicinoids.

2. Remarkably diastereoselective synthesis of a chiral biphenyl diphosphine ligand and its application in asymmetric hydrogenation.

3. Peptide-Catalyzed Fragment Couplings that Form Axially Chiral Non-C₂ -Symmetric Biaryls.

4. Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes.

5. Conversion of two stereocenters to one or two chiral axes: atroposelective synthesis of 2,3-diarylbenzoindoles.

Stereoselectivity of the benzannulation reaction: efficient central-to-axial chirality transfer.

1. Central-to-Axial Chirality Transfer in the Benzannulation Reaction of Optically Pure Fischer Carbene Complexes in the Synthesis of Allocolchicinoids.

2. Remarkably diastereoselective synthesis of a chiral biphenyl diphosphine ligand and its application in asymmetric hydrogenation.

3. Peptide-Catalyzed Fragment Couplings that Form Axially Chiral Non-C2 -Symmetric Biaryls.

4. Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes.

5. Conversion of two stereocenters to one or two chiral axes: atroposelective synthesis of 2,3-diarylbenzoindoles.

3. Peptide-Catalyzed Fragment Couplings that Form Axially Chiral Non-C₂ -Symmetric Biaryls.