135414-96-9

Basic information

• Product Name: 3-Butene-1,2-diol, 1-phenyl-, (1S,2R)-
• CAS NO: 135414-96-9
• Molecular Formula: C10H12O2
• Molecular Weight: 164.204
• Mol File: 135414-96-9.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 3-Butene-1,2-diol, 1-phenyl-, (1S,2R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Butene-1,2-diol, 1-phenyl-, (1S,2R)-(135414-96-9)
• EPA Substance Registry System: 3-Butene-1,2-diol, 1-phenyl-, (1S,2R)-(135414-96-9)

Safety Data

• Hazardous Substances Data: 135414-96-9(Hazardous Substances Data)

Upstream product

• 18295-60-8 allenylmagnesium bromide 
• 100-52-7 benzaldehyde 
• 62322-46-7 3-(1-methoxy-1-methylethoxy)prop-1-ene 
• 81656-05-5 2-methoxy-1-phenylbut-3-en-1-ol 
• 500757-14-2 C₁₇H₁₆O₃ 
• 106948-16-7 {Dimethyl-[(R)-1-((S)-phenyl-trimethylsilanyloxy-methyl)-allyl]-silanyl}-diisopropyl-amine 
• 1208092-25-4 prop-2-ene-1,1-diyl dibenzoate 
• 85677-20-9 threo-1-phenyl-2-(methoxymethoxy)-3-butenol 
• 82238-07-1 erythro-1-phenyl-2-(methoxymethoxy)-3-butenol 
• 18147-55-2 but-2-enyltrichlorosilane 
• 169517-16-2 2-allenyl-[1,3,2]-dioxaborinane 
• 1329020-55-4 C₁₃H₁₉BO₂ 
• 1329020-18-9 C₁₃H₁₉BO₂ 
• 167967-34-2 C₉H₁₇BO₂ 

Downstream Products

• 646995-81-5 (4S,5R)-2,2-dimethyl-4-phenyl-5-ethenyl[1,3]dioxolane 
• 155749-26-1 [(4R,5S)-2,2-dimethyl-5-phenyl[1,3]dioxolan-4-yl]methanol 

Relevant articles and documents

3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions

This account summarizes the development of new biheteroaromatic chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine oxides (BITIOPOs) have been successfully used as organocatalysts to promote Lewis base catalyzed, Lewis acid mediated stereoselective transformations. These highly electron-rich compounds, in combination with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride), generate hypervalent silicon species that act as chiral Lewis acids in highly diastereo- and enantioselective organic reactions. Several relevant examples related to these applications are discussed in detail. 1 Introduction 2 The BITIOPO Family 3 Enantioselective Opening of Epoxides 4 Enantioselective Allylation of Aldehydes 5 Stereoselective Direct (Double) Aldol-Type Reaction with Ketones 6 Stereoselective Direct Aldol-Type Reaction with Ester Derivatives 7 Conclusions.

Development of a double allylboration reagent targeting 1,5-syn-(E)-diols: Application to the synthesis of the C(23)-C(40) fragment of tetrafibricin

Interest in the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin prompted us to develop a new method for the synthesis of 1,5-syn-(E)-diols. Toward this end, the kinetically controlled hydroboration of allenes 6, 33, ent-39, 42, and 45 with the Soderquist borane 25R were studied. Tetrabutylammonium allenyltrifluoroborate 45 gave superior results and was utilized in a double allylboration sequence with two different aldehydes to provide the targeted 1,5-syn-(E)-diols in generally high yields (72-98%), and with high enantioselectivity (>95% ee), diastereoselectivity (dr >20:1), and (E)/(Z) selectivity (>20:1). This new method was applied to the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin.

Palladium-catalyzed synthesis of enantiomerically pure α-substituted allylboronic esters and their addition to aldehydes

Tartrate-derived boronic esters 2 can be subjected to palladium-catalyzed carbonyl allylations with SnCl2 to obtain enantiomerically pure α-substituted allylboronic esters 8 and 9. The reaction proceeds regioselectively and with high, simple diastereoselectivity to form anti-products. Their addition to aldehydes yields enantiomerically enriched homoallylic alcohols 17 and 18, respectively. Synthesis, characterization, and a mechanistic rational is presented here.