Chiral synthesis via organoboranes. 6. Asymmetric allylboration via chiral allyldialkylboranes. Synthesis of homoallylic alcohols with exceptionally high enantiomeric excess

Prabhakar K. Jadhav; Krishna S. Bhat; P. Thirumalai Perumal; Herbert C. Brown

doi:10.1021/jo00354a003

Chiral synthesis via organoboranes. 6. Asymmetric allylboration via chiral allyldialkylboranes. Synthesis of homoallylic alcohols with exceptionally high enantiomeric excess

The Journal of Organic Chemistry ◽

10.1021/jo00354a003 ◽

1986 ◽

Vol 51 (4) ◽

pp. 432-439 ◽

Cited By ~ 266

Author(s):

Prabhakar K. Jadhav ◽

Krishna S. Bhat ◽

P. Thirumalai Perumal ◽

Herbert C. Brown

Keyword(s):

Enantiomeric Excess ◽

Chiral Synthesis ◽

Homoallylic Alcohols

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ChemInform Abstract: Chiral Synthesis via Organoboranes. Part 5. Asymmetric Allylboration via Chiral Allyldialkylboranes. Synthesis of Homoallylic Alcohols with Exceptionally High Enantiomeric Excess

Chemischer Informationsdienst ◽

10.1002/chin.198634256 ◽

1986 ◽

Vol 17 (34) ◽

Author(s):

P. K. JADHAV ◽

K. S. BHAT ◽

P. T. PERUMAL ◽

H. C. BROWN

Keyword(s):

Enantiomeric Excess ◽

Chiral Synthesis ◽

Homoallylic Alcohols

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Application of a high-throughput enantiomeric excess optical assay involving a dynamic covalent assembly: parallel asymmetric allylation and ee sensing of homoallylic alcohols

Chemical Science ◽

10.1039/c5sc02416a ◽

2015 ◽

Vol 6 (12) ◽

pp. 6747-6753 ◽

Cited By ~ 29

Author(s):

H. H. Jo ◽

X. Gao ◽

L. You ◽

E. V. Anslyn ◽

M. J. Krische

Keyword(s):

High Throughput ◽

Enantiomeric Excess ◽

Parallel Synthesis ◽

Asymmetric Allylation ◽

Homoallylic Alcohols ◽

Optical Assay

Parallel synthesis and high-throughput ee screening.

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ChemInform Abstract: Chiral Synthesis via Organoboranes. Part 34. Selective Reductions. Part 47. Asymmetric Reduction of Hindered α,β-Acetylenic Ketones with B-Chlorodiisopinocampheylborane to Propargylic Alcohols of Very High Enantiomeric Excess. Improve

ChemInform ◽

10.1002/chin.199234068 ◽

2010 ◽

Vol 23 (34) ◽

pp. no-no

Author(s):

P. V. RAMACHANDRAN ◽

A. V. TEODOROVIC ◽

M. V. RANGAISHENVI ◽

H. C. BROWN

Keyword(s):

Asymmetric Reduction ◽

Enantiomeric Excess ◽

Chiral Synthesis ◽

Propargylic Alcohols ◽

Very High

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ChemInform Abstract: Chiral Synthesis via Organoboranes. Part 17. Preparation of α-Chiral α′-Alkynyl Ketones of High Enantiomeric Excess from Optically Pure Organyl(1-alkynyl)borinic Esters.

ChemInform ◽

10.1002/chin.198839171 ◽

1988 ◽

Vol 19 (39) ◽

Author(s):

H. C. BROWN ◽

A. K. GUPTA ◽

J. V. N. V. PRASAD ◽

M. SREBNIK

Keyword(s):

Enantiomeric Excess ◽

Chiral Synthesis ◽

Optically Pure

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Chiral synthesis via organoboranes. 10. Preparation of .alpha.-chiral acyclic ketones of exceptionally high enantiomeric excess from optically pure borinic esters

Journal of the American Chemical Society ◽

10.1021/ja00252a018 ◽

1987 ◽

Vol 109 (18) ◽

pp. 5420-5426 ◽

Cited By ~ 53

Author(s):

Herbert C. Brown ◽

Morris Srebnik ◽

Raman K. Bakshi ◽

Thomas E. Cole

Keyword(s):

Enantiomeric Excess ◽

Chiral Synthesis ◽

Acyclic Ketones ◽

Optically Pure

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ChemInform Abstract: Chiral Synthesis via Organoboranes. Part 10. Preparation of α-Chiral Acyclic Ketones of Exceptionally High Enantiomeric Excess from Optically Pure Borinic Esters.

ChemInform ◽

10.1002/chin.198751086 ◽

1987 ◽

Vol 18 (51) ◽

Author(s):

H. C. BROWN ◽

M. SREBNIK ◽

R. K. BAKSHI ◽

T. E. COLE

Keyword(s):

Enantiomeric Excess ◽

Chiral Synthesis ◽

Acyclic Ketones ◽

Optically Pure

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Chiral synthesis via organoboranes. 35. Simple procedures for the efficient recycling of the terpenyl chiral auxiliaries and convenient isolation of the homoallylic alcohols in asymmetric allyl- and crotylboration of aldehydes

The Journal of Organic Chemistry ◽

10.1021/jo00050a044 ◽

1992 ◽

Vol 57 (24) ◽

pp. 6608-6614 ◽

Cited By ~ 39

Author(s):

Herbert C. Brown ◽

Uday S. Racherla ◽

Y. Liao ◽

Vijay V. Khanna

Keyword(s):

Chiral Auxiliaries ◽

Chiral Synthesis ◽

Homoallylic Alcohols

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ChemInform Abstract: Chiral Synthesis via Organoboranes. Part 35. Simple Procedures for the Efficient Recycling of the Terpenyl Chiral Auxiliaries and Convenient Isolation of the Homoallylic Alcohols in Asymmetric Allyl- and Crotylboration of Aldehydes.

ChemInform ◽

10.1002/chin.199314054 ◽

2010 ◽

Vol 24 (14) ◽

pp. no-no

Author(s):

H. C. BROWN ◽

U. S. RACHERLA ◽

Y. LIAO ◽

V. V. KHANNA

Keyword(s):

Chiral Auxiliaries ◽

Chiral Synthesis ◽

Homoallylic Alcohols

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Chiral synthesis via organoboranes. 17. Preparation of .alpha.-chiral .alpha.'-alkynyl ketones of high enantiomeric excess from optically pure organyl(1-alkynyl)borinic esters

The Journal of Organic Chemistry ◽

10.1021/jo00242a009 ◽

1988 ◽

Vol 53 (7) ◽

pp. 1391-1394 ◽

Cited By ~ 23

Author(s):

Herbert C. Brown ◽

Ashok K. Gupta ◽

J. V. N. Vara Prasad ◽

Morris Srebnik

Keyword(s):

Enantiomeric Excess ◽

Chiral Synthesis ◽

Optically Pure

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Chiral synthesis via organoboranes. 34. Selective reductions. 47. Asymmetric reduction of hindered .alpha.,.beta.-acetylenic ketones with B-chlorodiisopinocampheylborane to propargylic alcohols of very high enantiomeric excess. Improved workup procedure for the isolation of product alcohols

The Journal of Organic Chemistry ◽

10.1021/jo00034a034 ◽

1992 ◽

Vol 57 (8) ◽

pp. 2379-2386 ◽

Cited By ~ 68

Author(s):

P. Veeraraghavan Ramachandran ◽

Aleksandar V. Teodorovic ◽

Milind V. Rangaishenvi ◽

Herbert C. Brown

Keyword(s):

Asymmetric Reduction ◽

Enantiomeric Excess ◽

Chiral Synthesis ◽

Propargylic Alcohols ◽

Alpha Beta ◽

Very High

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