90084-43-8

Basic information

• Product Name: (+)-PINANEBORANE
• Synonyms: (+)-PINANEBORANE;(+)-Pinanaborane;(1S,2S,3S,5S)-Pinanediol borane;Pinanediol borane
• CAS NO: 90084-43-8
• Molecular Formula: C₁₀H₁₇BO₂
• Molecular Weight: 180.05
• Mol File: 90084-43-8.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerated.
• Solubility: Chloroform (Slightly), Toluene (Sparingly)
• Stability: Moisture and Air Sensitive
• CAS DataBase Reference: (+)-PINANEBORANE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-PINANEBORANE(90084-43-8)
• EPA Substance Registry System: (+)-PINANEBORANE(90084-43-8)

Safety Data

• Hazardous Substances Data: 90084-43-8(Hazardous Substances Data)

Usage

Uses

(+)-Pinanediol Borane is a chiral catalyst used in the synthesis of N-acyl L-amino acids.

Upstream product

• 18680-27-8 pinanediol 
• 13292-87-0 dimethyl sulfide borane 

Downstream Products

• 612836-12-1 (dimethylphenylsilyl)((+)-pinanediolato)borane 
• 90084-38-1 (+)-pinanediol 3-benzyloxypropaneboronate 
• 90084-37-0 (3aS,4S,6S,7aR)-2-(3-bromopropyl)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole 

Relevant articles and documents

Hydroboronation process

The invention relates to processes for the synthesis of aryl or alkene borates which comprises reacting: (i) an olefinic compound having a halogen or halogen-like substituent in a vinylic substitution position, or (ii) an aromatic ring having a halogen or halogen-like substituent in a ring substitution position, with a disubstituted monohydroborane in the presence of a Group 8-11 metal catalyst. The invention also relates to the use of these borates in coupling reactions. The invention further relates to certain disubstituted monohydroboranes and aryl or alkene borates.

Synthesis and properties of pinanediol α-amido boronic esters

The use of (+)-pinanediol as the chiral directing group for the synthesis of several α(R)-α-amido boronic esters and acids, which are boronic acid analogues of N-acyl-L-amino acids, has been explored. RBO2Pin (Pin = cis-pinane-2,3-diyl) was homologated to (S)-RCHClBO2Pin, which was converted to (R)-RCH-(NHAc)BO2Pin and, for R = isopropyl, to (R)-RCH(NHCOAc)B(OH)2 by previously reported methods. Where R = isobutyl, methyl, or (benzyloxy)methyl, zinc chloride catalysis was required for the homologation step. Two (S)-acetamido boronic esters (R = isopropyl, isobutyl) were made from (-)-pinanediol. Acylation of the unstable α-amino boronic ester intermediate with carbobenzyloxy chloride was accomplished in the synthesis of PhCH2CH(NHCOOCH2Ph)BO2Pin, but attempted boron trichloride cleavage of the pinanediol boronic ester to the acid also cleaved the benzyloxy group. Hydroboration of allyl halides or allyl benzyl ether with (1,2-phenyldioxy)borane has yielded γ-substituted boronic esters. These were converted to (+)-pinanediol esters and converted by the general route outlined above to α-acetamido δ-substituted boronic esters. (Pinanediyldioxy)borane has been prepared and found to be a sluggish hydroborating agent.