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H. Brown, M. Srebnik, P. Ramachandran (1989)
Chiral synthesis via organoboranes. 22. Selective reductions. 44. The effect of the steric requirements of the alkyl substituent in isopinocampheylalkylchloroboranes for the asymmetric reduction of representative ketonesJournal of Organic Chemistry, 54
J. Westley, B. Halpern (1968)
The use of /-/-menthyl chloroformate in the optical analysis of asymmetric amino and hydroxyl compounds by gas chromatography.Journal of Organic Chemistry, 33
H. Brown, R. Holmes (1956)
The Heats of Reaction of Pyridine and Nitrobenzene with Boron Trifluoride, Trichloride and Tribromide; the Relative Acceptor Properties of the Boron Halides1,2Journal of the American Chemical Society, 78
H. Brown, B. Singaram (1984)
Hydroboration. 68. Chiral synthesis via organoboranes. 1. A simple procedure to achieve products of essentially 100% optical purity in hydroboration of alkenes with monoisopinocampheylborane. Synthesis of boronic esters and derived products of very high enantiomeric puritiesJournal of the American Chemical Society, 106
H. Brown, S. Kulkarni (1979)
Organoboranes : XXIV. Facile substitution and exchange reactions of 9-borabicyclo[3.3.1]nonane (9-BBN) and its B-substituted derivatives. Simple convenient preparations of B-halo derivatives☆Journal of Organometallic Chemistry, 168
H. Brown, J. Sikorski (1982)
Organoboranes. 26. Boron-11 NMR investigation of reactions of 2,3-dimethyl-2-butene with monochloroborane complexes. Preparation and hydroboration characteristics of thexylchloroborane reagentsOrganometallics, 1
H. Brown, W. Park, B. Cho, P. Ramachandran (1987)
Selective reductions. 40. A critical examination of the relative effectiveness of various reducing agents for the asymmetric reduction of different classes of ketonesJournal of Organic Chemistry, 52
H. Brown, N. Ravindran (1976)
Hydroboration. XL. Hydroboration of alkenes and alkynes with monochloroborane etherates. Convenient procedures for the preparation of dialkyl-, monoalkyl-, and dialkenylchloroboranes and their derivativesJournal of the American Chemical Society, 98
N. Joshi, M. Srebnik, H. Brown (1988)
Enantioselective ring cleavage of meso-epoxides with B-halodiisopinocampheylboranes.Journal of the American Chemical Society, 110 18
P. McCusker, H. Makowski (1957)
Organoboron Compounds. IV. Phenyldifluoroborane and Other Aryldihalogenoboranes1-3Journal of the American Chemical Society, 79
M. Srebnik, N. Joshi, H. Brown (1989)
Chiral Synthesis via Organoboranes 23. Enantioselective Ring Opening of meso‐Epoxides with B‐Halodiisopinocampheylboranes. The First General Synthesis of Optically Active 1,2‐HalohydrinsIsrael Journal of Chemistry, 29
K. Kinberger, W. Siebert (1975)
Synthese und Eigenschaften von Dimethylsulfan-Halogenboranen, (CH3)2SBHnX3-n / Synthesis and Properties of Dimethylsulfane-haloboranes, (CH3)2SBHnX3-nZeitschrift für Naturforschung B, 30
N. Joshi, C. Pyun, V. Mahindroo, B. Singaram, H. Brown (1992)
Chiral Synthesis via Organoboranes. 33. The Controlled Reaction of B- Alkydiisopinocampheylboranes with Aldehydes Providing a Convenient Procedure for the Enantiomeric Enrichment of the Boronic Ester Products Through Kinetic ResolutionJournal of Organic Chemistry, 57
A. King, E. Corley, R. Anderson, R. Larsen, T. Verhoeven, P. Reider, X. Bin, M. Belley, Y. Leblanc (1993)
An efficient synthesis of LTD4 antagonist L-699,392Journal of Organic Chemistry, 58
H. Brown, B. Singaram (1984)
Improved procedures for the synthesis of diisopinocampheylborane of high optical purityJournal of Organic Chemistry, 49
H. C. Brown, P. V. Ramachandran
Advances in Asymmetric Synthesis
J. Chandrasekharan, P. Ramachandran, H. Brown (1985)
Diisopinocampheylchloroborane, a remarkably efficient chiral reducing agent for aromatic prochiral ketonesJournal of Organic Chemistry, 50
H. Brown, M. Rei (1966)
A Convenient Procedure for the Quantitative Conversion of Reactive Alcohols and Olefins into the Corresponding ChloridesJournal of Organic Chemistry, 31
T. Imai, T. Tamura, A. Yamamuro, Tsuneo Sato, T. Wollmann, R. Kennedy, S. Masamune (1986)
Organoboron compounds in organic synthesis. 2. Asymmetric reduction of dialkyl ketones with (R,R)- or (S,S)-2,5-dimethylborolaneJournal of the American Chemical Society, 108
H. Brown, N. Ravindran (1977)
Monochloroborane-methyl sulfide, H2BCl.S(CH3)2, and dichloroborane-methyl sulfide, HBCl2.S(CH3)2, as new stable hydroborating agents with high regiospecificityJournal of Organic Chemistry, 42
H. Brown, J. Chandrasekharan, P. Ramachandran (1988)
Chiral synthesis via organoboranes. 14. Selective reductions. 41. Diisopinocampheylchloroborane, an exceptionally efficient chiral reducing agentJournal of the American Chemical Society, 110
M. Midland, S. Greer, A. Tramontano, S. Zderic (1979)
Chiral trialkylborane reducing agents. Preparation of 1-deuterio primary alcohols of high enantiomeric purityJournal of the American Chemical Society, 101
H. Brown, P. Ramachandran (1992)
Asymmetric reduction with chiral organoboranes based on .alpha.-pineneAccounts of Chemical Research, 25
M. Midland, D. McDowell, R. Hatch, A. Tramontano (1980)
Reduction of .alpha.,.beta.-acetylenic ketones with B-3-pinanyl-9-borabicyclo[3.3.1]nonane. High asymmetric induction in aliphatic systemsJournal of the American Chemical Society, 102
E. Corey, R. Bakshi, S. Shibata (1987)
Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines. Mechanism and synthetic implicationsJournal of the American Chemical Society, 109
M. Midland, J. Petre, S. Zderic, A. Kazubski (1982)
Thermal reactions of B-alkyl-9-borabicyclo[3.3.1]nonane (9-BBN). Evidence for unusually facile dehydroboration with B-pinanyl-9-BBNJournal of the American Chemical Society, 104
J. Dale, D. Dull, H. Mosher (1969)
.alpha.-Methoxy-.alpha.-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and aminesJournal of Organic Chemistry, 34
S. Itsuno, Yoshiki Sakurai, Koichi Ito, A. Hirao, S. Nakahama (1987)
Catalytic Behavior of Optically Active Amino Alcohol–Borane Complex in the Enantioselective Reduction of Acetophenone Oxime O-Alkyl EthersBulletin of the Chemical Society of Japan, 60
H. Brown, P. Jadhav (1983)
Asymmetric carbon-carbon bond formation via .beta.-allyldiisopinocampheylborane. Simple synthesis of secondary homoallylic alcohols with excellent enantiomeric puritiesJournal of the American Chemical Society, 105
H. Brown, G. Pai, P. Jadhav (1984)
Remarkable optical induction in the reduction of .alpha.-oxo esters with B-(3-pinanyl)-9-borabicyclo[3.3.1]nonane. Synthesis of .alpha.-hydroxy esters of 100% optical purityJournal of the American Chemical Society, 106
P. Ramachandran, A. Teodorović, M. Rangaishenvi, H. Brown (1992)
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 alcoholsJournal of Organic Chemistry, 57
R. Soundararajan, D. Matteson (1990)
Hydroboration with boron halides and trialkylsilanesJournal of Organic Chemistry, 55
H. Brown, N. Ravindran, S. Kulkarni (1979)
HYDROBORATION. 52. MONOHALOBORANE-METHYL SULFIDE ADDUCTS AS NEW REAGENTS FOR THE HYDROBORATION OF ALKENES. A CONVENIENT SYNTHESIS OF DIALKYLHALOBORANES AND THEIR DERIVATIVES FOR ORGANIC SYNTHESISChemInform, 10
Gerhard Bir, D. Kaufmann (1987)
Synthese von isopinocampheylhalogenboranen und ihre verwendung als chirale katalysatoren für asymmetrische diels-alder-reaktionenTetrahedron Letters, 28
H. Brown, B. Cho, W. Park (1988)
Chiral synthesis via organoboranes. 15. Selective reductions. 42. Asymmetric reduction of representative prochiral ketones with potassium 9-O-(1,2:5,6-di-O-isopropylidene-.alpha.-D-glucofuranosyl)-9-boratabicyclo[3.3.1]nonaneJournal of Organic Chemistry, 53
H. Brown, G. Pai (1983)
Asymmetric reduction of prochiral .alpha.-halo ketones with B-3-pinanyl-9-borabicyclo[3.3.1]nonaneJournal of Organic Chemistry, 48
P. Ramachandran, H. Brown, S. Swaminathan (1990)
Lithium-B-Iso-2-ethylapopinocampheyl-9-borabicyclo[3.3.1]nonyl hydride as an improved reagent for asymmetric reduction of unhindered aliphatic ketones. Further evidence for the improved enantioselectivity in reductions by reagents containing increased steric requirements at the 2-position of the apoTetrahedron-asymmetry, 1
H. Brown, J. Chandrasekharan, P. Ramachandran (1986)
Highly efficient asymmetric reduction of .alpha.-tertiary alkyl ketones with diisopinocampheylchloroboraneJournal of Organic Chemistry, 51
A series of diisopinocampheylhaloboranes and monoisopinocampheyldihaloboranes were synthesized by the reaction of the corresponding boranes with the respective HX or X2 (X = halogen) or by the hydroboration of α‐pinene with the corresponding haloboranes. Stabilities of these haloboranes in various solvents were studied. Most of these haloboranes proved capable of reducing prochiral ketones to the alcohols with significant optical induction. When tested against a representative aromatic and aliphatic prochiral ketone, acetophenone and 3‐methyl‐2‐butanone, respectively, α‐phenethyl alcohol in 65–98% ee and 3‐methyl‐2‐butanol in 28–59% ee were obtained. Some of them exhibited anomalous behavior.
Heteroatom Chemistry – Wiley
Published: Jan 1, 1995
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