Organocyanocopper-trifluoroborane mediated 1,3-chirality transfer reaction of .gamma.-(mesyloxy)-.alpha.-alkyl .alpha.,.beta.-enoates for the construction of chiral quaternary carbon centers with high optical purity

Toshiro Ibuka; Naoshige Akimoto; Miwa Tanaka; Shinji Nishii; Yoshinori Yamamoto

doi:10.1021/jo00278a015

Organocyanocopper-trifluoroborane mediated 1,3-chirality transfer reaction of .gamma.-(mesyloxy)-.alpha.-alkyl .alpha.,.beta.-enoates for the construction of chiral quaternary carbon centers with high optical purity

The Journal of Organic Chemistry ◽

10.1021/jo00278a015 ◽

1989 ◽

Vol 54 (17) ◽

pp. 4055-4061 ◽

Cited By ~ 45

Author(s):

Toshiro Ibuka ◽

Naoshige Akimoto ◽

Miwa Tanaka ◽

Shinji Nishii ◽

Yoshinori Yamamoto

Keyword(s):

Transfer Reaction ◽

Optical Purity ◽

Quaternary Carbon ◽

Chirality Transfer ◽

Carbon Centers ◽

High Optical Purity ◽

Alpha Beta

Download Full-text

ChemInform Abstract: Organocyanocopper-Trifluoroborane-Mediated 1,3-Chirality Transfer Reaction of γ-(Mesyloxy) α-Alkyl α,β-Enoates for the Construction of Chiral Quaternary Carbon Centers with High Optical Purity.

ChemInform ◽

10.1002/chin.199005221 ◽

1990 ◽

Vol 21 (5) ◽

Author(s):

T. IBUKA ◽

N. AKIMOTO ◽

M. TANAKA ◽

S. NISHII ◽

Y. YAMAMOTO

Keyword(s):

Transfer Reaction ◽

Optical Purity ◽

Quaternary Carbon ◽

Chirality Transfer ◽

Carbon Centers ◽

High Optical Purity

Download Full-text

An efficient synthesis of chiral quaternary carbon centres with high optical purity via 1,3-chirality transfer

Journal of the Chemical Society Chemical Communications ◽

10.1039/c39870001596 ◽

1987 ◽

pp. 1596 ◽

Cited By ~ 21

Author(s):

Toshiro Ibuka ◽

Miwa Tanaka ◽

Shinji Nishii ◽

Yoshinori Yamamoto

Keyword(s):

Optical Purity ◽

Efficient Synthesis ◽

Quaternary Carbon ◽

Chirality Transfer ◽

High Optical Purity

Download Full-text

Very high chemoselective, regioselective, and E-stereoselective 1,3-chirality transfer involving reaction of acyclic (E)- and (Z)-.gamma.-mesyloxy .alpha.,.beta.-enoates and organocyanocopper-trifluoroborane reagents. Efficient synthetic routes to functionalized chiral .alpha.-alkyl (E)-.beta.,.gamma.-enoates and (E)-allylic alcohols with high optical purity

Journal of the American Chemical Society ◽

10.1021/ja00195a045 ◽

1989 ◽

Vol 111 (13) ◽

pp. 4864-4872 ◽

Cited By ~ 51

Author(s):

Toshiro Ibuka ◽

Miwa Tanaka ◽

Shinji Nishii ◽

Yoshinori Yamamoto

Keyword(s):

Optical Purity ◽

Allylic Alcohols ◽

Chirality Transfer ◽

High Optical Purity ◽

Synthetic Routes ◽

Alpha Beta ◽

Very High

Download Full-text

ChemInform Abstract: An Efficient Synthesis of Chiral Quaternary Carbon Centres with High Optical Purity via 1,3-Chirality Transfer.

ChemInform ◽

10.1002/chin.198812093 ◽

1988 ◽

Vol 19 (12) ◽

Author(s):

T. IBUKA ◽

M. TANAKA ◽

S. NISHII ◽

Y. YAMAMOTO

Keyword(s):

Optical Purity ◽

Efficient Synthesis ◽

Quaternary Carbon ◽

Chirality Transfer ◽

High Optical Purity

Download Full-text

New Amino Acids for the Topographical Control of Peptide Conformation: Synthesis of All the Isomers of .alpha.,.beta.-Dimethylphenylalanine and .alpha.,.beta.-Dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid of High Optical Purity

The Journal of Organic Chemistry ◽

10.1021/jo00086a033 ◽

1994 ◽

Vol 59 (7) ◽

pp. 1789-1795 ◽

Cited By ~ 39

Author(s):

Wieslaw M. Kazmierski ◽

Zofia Urbanczyk-Lipkowska ◽

Victor J. Hruby

Keyword(s):

Amino Acids ◽

Carboxylic Acid ◽

Optical Purity ◽

Peptide Conformation ◽

High Optical Purity ◽

Alpha Beta

Download Full-text

Higher order zinc cuprate reagents. Very high 1,3-chirality transfer reaction of .gamma.-(mesyloxy)-.alpha.,.beta.-unsaturated carbonyl derivatives

The Journal of Organic Chemistry ◽

10.1021/jo00029a048 ◽

1992 ◽

Vol 57 (3) ◽

pp. 1024-1026 ◽

Cited By ~ 36

Author(s):

Yoshinori Yamamoto ◽

Miwa Tanaka ◽

Toshiro Ibuka ◽

Yukiyasu Chounan

Keyword(s):

Transfer Reaction ◽

Higher Order ◽

Chirality Transfer ◽

Carbonyl Derivatives ◽

Alpha Beta ◽

Very High

Download Full-text

Copper-Catalyzed Decarboxylative [3 + 2] Annulation of Ethynylethylene Carbonates with Azlactones: Access to γ-Butyrolactones Bearing Two Vicinal Quaternary Carbon Centers

The Journal of Organic Chemistry ◽

10.1021/acs.joc.0c02621 ◽

2020 ◽

Author(s):

Wen-Ya Lu ◽

Yun Wang ◽

Yong You ◽

Zhen-Hua Wang ◽

Jian-Qiang Zhao ◽

...

Keyword(s):

Quaternary Carbon ◽

Carbon Centers

Download Full-text

ChemInform Abstract: Trapping of Oxonium Ylide with Isatins: Efficient and Stereoselective Construction of Adjacent Quaternary Carbon Centers.

ChemInform ◽

10.1002/chin.200812116 ◽

2008 ◽

Vol 39 (12) ◽

Author(s):

Xin Guo ◽

Haoxi Huang ◽

Liping Yang ◽

Wenhao Hu

Keyword(s):

Quaternary Carbon ◽

Carbon Centers ◽

Oxonium Ylide

Download Full-text

Stereocontrolled Synthesis of Highly Functionalized Quaternary Carbon Centers: A Route to α-Substituted Serines

Angewandte Chemie ◽

10.1002/ange.200900609 ◽

2009 ◽

Vol 121 (23) ◽

pp. 4266-4269 ◽

Cited By ~ 4

Author(s):

Xavier Ariza ◽

Josep Cornellà ◽

Mercè Font-Bardia ◽

Jordi Garcia ◽

Jordi Ortiz ◽

...

Keyword(s):

Quaternary Carbon ◽

Carbon Centers ◽

Stereocontrolled Synthesis

Download Full-text

Electrochemically-initiated Michael addition of chiral acetoacetic derivatives to methyl vinyl ketone: stereocontrolled construction of quaternary carbon centers

Tetrahedron Asymmetry ◽

10.1016/s0957-4166(02)00636-5 ◽

2002 ◽

Vol 13 (21) ◽

pp. 2311-2316 ◽

Cited By ~ 15

Author(s):

Laura Palombi ◽

Marta Feroci ◽

Monica Orsini ◽

Achille Inesi

Keyword(s):

Michael Addition ◽

Vinyl Ketone ◽

Methyl Vinyl Ketone ◽

Quaternary Carbon ◽

Methyl Vinyl ◽

Carbon Centers

Download Full-text