202589-95-5

Upstream product

• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 18147-55-2 (E)-crotyltrichlorosilane 
• 100-52-7 benzaldehyde 
• 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 
• 675834-57-8 (1S,2S)-1-phenyl-1-(tert-butyldimethylsilyloxy)but-3-en-2-ol 
• 474958-70-8 (1S,2S)-2-(2-methoxy-ethoxymethoxy)-1-phenyl-but-3-en-1-ol 

Downstream Products

• 474958-88-8 [(1R)-1-((4S,5S)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-but-3-enyl]-3-phenyl prop-2-enoate 
• 474958-89-9 (6R)-6-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5,6-dihydro-2H-pyran-2-one 
• 153481-85-7 (4R,5S)-2,2-dimethyl-5-phenyl-[1,3]-dioxolane-4-carbaldehyde 
• 146236-73-9 (6R)-6-[(1R,2S)-1,2-dihydroxy-2-phenylethyl]-5,6-dihydro-2H-pyran-2-one 
• 136685-37-5 (1R,5R,7S,8S)-8-hydroxy-7-phenyl-2,6-dioxa-bicyclo-[3.3.1]-nonan-3-one 
• 153609-00-8 (4S,5S)-2,2-dimethyl-4-(hydroxymethyl)-5-phenyl-1,3-dioxolane 
• 474958-86-6 (4S,5S)-2,2-dimethyl-4-phenyl-5-ethenyl[1,3]dioxolane 

Relevant academic research and scientific papers

Arabinose as a chiral auxiliary for the asymmetric α-hydroxyallylation of aldehydes to syn-1,2-diols

In de presence of triethylaluminum, enantiomerically pure syn-1-substituted-3-butene-1,2-diol derivatives 4 are synthesized stereoselectively starting from allyl arabinopyranoside 3 and aldehydes.

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.

Enantio- and diastereoselective synthesis of (E)-1,5-syn-diols: Application to the synthesis of the C(23)-C(40) fragment of tetrafibricin

A highly stereoselective synthesis of (E)-1,5-syn-diols 6 is described. The kinetically controlled hydroboration of allenyltrifluoroborate 8 with Soderquist borane 2 provides the (Z)-allylic trifluoroborate 9, which undergoes sequential allylboration with two different aldehydes to provide (E)-1,5-syn-diols 6 in 72-98% yields with >95% ee and >20:1 dr. Application of this method to the synthesis of the tetrafibricin C(23)-C(40) fragment 19 is described.

Revision of stereochemical assignments of (2,2-dimethyl-5-phenyl-[1,3] dioxolan-4-yl)-methanol

Opposite signs of specific rotation are reported in the literature for (4S,5S)-(2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-methanol. The correct assignment was made by unambiguous synthesis of the title compound via the reaction of (S)-O-TBS-mandelic aldeh

Stereoselective syntheses of (+)-goniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone via alkoxyallylboration and ring-closing metathesis

A convenient synthesis of (+)-goniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone has been developed via asymmetric alkoxyallylboration and ring-closing metathesis pathways.

A short and general approach to the synthesis of styryllactones: (+)-Goniodiol, its acetates and β-trifluoromethyl derivative, (+)-7-epi-Goniodiol and (+)-9-deoxygoniopypyrone

(+)-Goniodiol, its acetates and β-trifluoromethyl derivative, (+)-7-epi-Goniodiol and (+)-9-deoxygoniopypyrone, the representatives of styryllactones have been synthesized in a short and general way. The key steps involve the regioselective asymmetric dihydroxylation and the palladium-catalyzed cross-coupling of cyclic allylic carbonate with vinyltributylstannane.