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

Toshiro Ibuka; Miwa Tanaka; Shinji Nishii; Yoshinori Yamamoto

doi:10.1021/ja00195a045

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

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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

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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

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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

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ChemInform Abstract: Chiral Synthesis via Organoboranes. Part 20. Conversion of Boronic Esters of Essentially 100% Optical Purity to B-Alkyl-9-borabicyclo(3.3.1)nonanes of Very High Optical Purity. Synthesis of Optically Active Homologated Esters, Nitrile

ChemInform ◽

10.1002/chin.198923060 ◽

1989 ◽

Vol 20 (23) ◽

Author(s):

H. C. BROWN ◽

N. N. JOSHI ◽

C. PYUN ◽

B. SINGARAM

Keyword(s):

Optical Purity ◽

Optically Active ◽

Chiral Synthesis ◽

High Optical Purity ◽

Boronic Esters ◽

Very High

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ChemInform Abstract: CHIRAL SYNTHESIS VIA ORGANOBORANES. 2. RAPID REACTION OF BORONIC ESTERS OF VERY HIGH OPTICAL PURITY WITH LITHIUM ALUMINUM HYDRIDE. FACILE REACTION OF ESSENTIALLY OPTICALLY PURE BORINIC ESTERS WITH LITHIUM MONOETHOXYALUMINOHYDRIDE. A N

Chemischer Informationsdienst ◽

10.1002/chin.198521284 ◽

1985 ◽

Vol 16 (21) ◽

Author(s):

H. C. BROWN ◽

B. SINGARAM ◽

T. E. COLE

Keyword(s):

Lithium Aluminum Hydride ◽

Optical Purity ◽

Aluminum Hydride ◽

Lithium Aluminum ◽

Chiral Synthesis ◽

High Optical Purity ◽

Boronic Esters ◽

Rapid Reaction ◽

Optically Pure ◽

Very High

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Chiral synthesis via organoboranes. 12. Conversion of boronic esters of essentially 100% optical purity into monoalkylthexylboranes providing convenient synthetic routes to trans-olefins, cis-olefins, alkynes, and ketones of very high enantiomeric purities

Journal of the American Chemical Society ◽

10.1021/ja00213a028 ◽

1988 ◽

Vol 110 (5) ◽

pp. 1529-1534 ◽

Cited By ~ 40

Author(s):

Herbert C. Brown ◽

Raman K. Bakshi ◽

Bakthan. Singaram

Keyword(s):

Optical Purity ◽

Chiral Synthesis ◽

Boronic Esters ◽

Synthetic Routes ◽

Very High

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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

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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

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A highly efficient synthesis of γ-halo allylic alcohols and propargylic alcohols with high optical purity. Practical method for synthesis of the prostaglandin ω-chain

Tetrahedron Letters ◽

10.1016/s0040-4039(00)96038-6 ◽

1987 ◽

Vol 28 (18) ◽

pp. 2033-2036 ◽

Cited By ~ 42

Author(s):

Sentaro Okamoto ◽

Toshiyuki Shimazaki ◽

Yuichi Kobayashi ◽

Fumie Sato

Keyword(s):

Optical Purity ◽

Practical Method ◽

Allylic Alcohols ◽

Efficient Synthesis ◽

Propargylic Alcohols ◽

Highly Efficient ◽

High Optical Purity

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ChemInform Abstract: Very High Chemoselective, Regioselective, and E-Stereoselective 1,3-Chirality Transfer Involving Reaction of Acyclic (E)- and (Z)-γ-Mesyloxy α,β-Enoates and Organocyanocopper-Trifluoroborane Reagents. Efficient Synthetic Routes to Fun

ChemInform ◽

10.1002/chin.198940075 ◽

1989 ◽

Vol 20 (40) ◽

Author(s):

T. IBUKA ◽

M. TANAKA ◽

S. NISHII ◽

Y. YAMAMOTO

Keyword(s):

Chirality Transfer ◽

Synthetic Routes ◽

Very High

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