Rhodium-Catalyzed Asymmetric Allenylation of Sulfonylimines and Application to the Stereospecific Allylic Allenylation

被引：17

作者：

Sieber, Joshua D. ^{[1
]}

Angeles-Dunham, Veronica V. ^{[2
]}

Chennamadhavuni, Divya ^{[3
]}

Fandrick, Daniel R. ^{[1
]}

Haddad, Nizar ^{[1
]}

Grinberg, Nelu ^{[1
]}

Kurouski, Dimitry ^{[1
]}

Lee, Heewon ^{[1
]}

Song, Jinhua J. ^{[1
]}

Yee, Nathan K. ^{[1
]}

Mattson, Anita E. ^{[2
]}

Senanayake, Chris H. ^{[1
]}

机构：

[1] Boehringer Ingelheim Pharmaceut Inc, Dept Chem Dev, 900 Ridgebury Rd,POB 368, Ridgefield, CT 06877 USA

[2] Ohio State Univ, Dept Chem & Biochem, Columbus, OH 43210 USA

[3] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 19期

关键词：

allylic alkylation; asymmetric allenylation; palladium; phosphorus ligands; rhodium; N-TOSYLARYLIMINES; ENANTIOSELECTIVE SYNTHESIS; COUPLING-CYCLIZATION; ORGANOBORONIC ACIDS; EFFICIENT SYNTHESIS; ARYLBORONIC ACIDS; AMINO ALLENES; CHIRAL LIGAND; ALPHA-AMINO; SUBSTITUTION;

D O I：

10.1002/adsc.201600686

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The rhodium-catalyzed asymmetric allenylation of sulfonylimines is disclosed providing silyl homoallenylamide products in up to 99:1 er. Through subsequent activation of the C-N bond of the silyl homoallenyl sulfonamide, palladium-catalyzed stereospecific allylic allenylation could be achieved giving C-C bond formation with high chirality transfer. The synthetic utility of both the silyl homoallenyl sulfonamides and the silyl homoallenyl malonates as bis(nucleophiles) is demonstrated.

引用

页码：3062 / 3068

页数：7

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