Abstract: The present invention relates to a borane ether complex of the formula 1, wherein R1 to R4 represent independently from each other hydrogen, C1-C4-alkyl, C3-C6-cycloalkyl or a substituent of the formula CH2OR5, wherein R5 is C1-C4-alkyl or C3-C6-cycloalkyl, or two adjacent substituents R1 to R4 together are a divalent group selected from the group consisting of —CH2CH2—, —CH(CH3)CH2—, —CH2CH2CH2—, —CH(CH3)CH(CH3)—, —CH(CH2CH3)CH2—, —C(CH3)2C(CH3)2—, —CH2C(CH3)2CH2— and —(CH2)6— to form with the —CH—CH— moiety of the tetrahydrofuran ring a cyclic structure, with the provision that at least one of the substituents R1 to R4 is not hydrogen. The invention also relates to a method of using new borane complexes with substituted tetrahydrofuran ethers for organic reactions.

Abstract: A method of increasing enantioselectivity in a reduction reaction of a prochiral substrate with a borane reagent including a borohydride species (for example, a borohydride stabilized borane-tetrahydrofuran complex) catalyzed by a chiral catalyst includes the step of maintaining the concentration of borohydride species in the borane reagent below approximately 0.005 M during the reduction of the prochiral substrate. A method of increasing enantioselectivity in a reduction reaction of a prochiral substrate with a borane reagent including a borohydride species that is catalyzed by a chiral catalyst includes the step of reducing the detrimental effect the borohydride species has on enantioselectivity by adding a Lewis acid. For example, the prochiral substrate can be a ketone and the chiral catalyst can be a chiral oxazaborolidine.

Abstract: A method for synthesizing highly soluble metal alkoxides includes the step of reacting a tertiary alcohol having the formula: 1

Abstract: A method for synthesizing highly soluble metal alkoxides includes the step of reacting a tertiary alcohol having the formula: wherein R1, R2, and R3 are, independently, the same or different, an alkyl group, an alkenyl, an alkynyl group or an aryl group, and at least one of R1, R2, and R3 is a group of at least 3 carbon atoms, with at least a stoichiometric amount of a metal reagent. The metal reagent is generally a group I metal, a group II metal, zinc, a metal alloy of a group I metal, a metal alloy of a group II metal, a metal alloy of zinc, a compound of a group I metal, a compound of a group II metal or a compound of zinc.

Abstract: A method of increasing enantioselectivity in a reduction reaction of a prochiral substrate with a borane reagent including a borohydride species (for example, a borohydride stabilized borane-tetrahydrofuran complex) catalyzed by a chiral catalyst includes the step of maintaining the concentration of borohydride species in the borane reagent below approximately 0.005 M during the reduction of the prochiral substrate. A method of increasing enantioselectivity in a reduction reaction of a prochiral substrate with a borane reagent including a borohydride species that is catalyzed by a chiral catalyst includes the step of reducing the detrimental effect the borohydride species has on enantioselectivity by adding a Lewis acid. For example, the prochiral substrate can be a ketone and the chiral catalyst can be a chiral oxazaborolidine.

Abstract: A synthetic route for forming lithium trisubstituted borohydride compounds comprises the step of reacting a processed lithium hydride reactant with a trisubstituted borane wherein the reaction is maintained for a period of time in a temperature range of approximately 15° C. to approximately 42° C. A method of synthesizing LiH comprises the step of reacting an alkyl lithium (for example, n-butyl lithium) with hydrogen in the presence of tetrahydrofuran. The reaction temperature is preferably maintained in the range of approximately −78° C. to approximately 25° C.

Abstract: A synthetic route for forming lithium trisubstituted borohydride compounds comprises the step of reacting a processed lithium hydride reactant with a trisubstituted borane wherein the reaction is maintained for a period of time in a temperature range of approximately 15° C. to approximately 42° C. A method of synthesizing LiH comprises the step of reacting an alkyl lithium (for example, n-butyl lithium) with hydrogen in the presence of tetrahydrofuran. The reaction temperature is preferably maintained in the range of approximately −78° C. to approximately 25° C.

Abstract: A method of increasing enantioselectivity in a reduction reaction of a prochiral substrate with a borane reagent including a borohydride species (for example, a borohydride stabilized borane-tetrahydrofuran complex) catalyzed by a chiral catalyst includes the step of maintaining the concentration of borohydride species in the borane reagent below approximately 0.005 M during the reduction of the prochiral substrate. A method of increasing enantioselectivity in a reduction reaction of a prochiral substrate with a borane reagent including a borohydride species that is catalyzed by a chiral catalyst includes the step of reducing the detrimental effect the borohydride species has on enantioselectivity by adding a Lewis acid. For example, the prochiral substrate can be a ketone and the chiral catalyst can be a chiral oxazaborolidine.

Abstract: A method of stabilizing borane-tetrahydrofuran complex comprises the step of maintaining the temperature of the borane-tetrahydrofuran complex at or below 20.degree. C. A method of reacting a borane reagent with a substrate comprises the steps of heating the borane reagent and the substrate in a reaction vessel and preventing escape of evolved diborane from the reaction vessel. Preferably, a reaction vessel containing a borane reagent and a substrate is maintained under at greater than atmospheric pressure with back-pressure regulation.

Abstract: A one-step process is provided for the synthesis of organohaloboranes, including diisopinocampheylchloroborane, and alkoxyorganoboranes. The present process does not utilize a thermally unstable ether adduct or a malodorous dimethyl sulfide adduct as required in prior processes. In general, the organohaloboranes are synthesized in a single reactor by reacting olefin(s) and/or alkyne(s) with boron trihalide and diborane. Alkoxyorganoboranes are synthesized in a single reactor by reacting olefin(s) and/or alkyne(s) with alkylborate and diborane.