133271-05-3

Upstream product

• 652993-72-1 (6S,3Z)-ethyl 6-hydroxy-6-phenylhex-3-enoate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 112635-77-5 ethyl (S)-(-)-3-(tert-butyldimethylsilyloxy)-3-phenylpropanoate 
• 33401-74-0 ethyl (3R)-3-hydroxy-3-phenylpropionate 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 794525-13-6 (4S)-3-[(2E,5S)-5-hydroxy-2-methyl-5-phenylpent-2-enoyl]-4-isopropyloxazolidin-2-one 
• 77118-87-7 (S)-1-Phenyl-3-buten-1-ol 
• 100-52-7 benzaldehyde 

Downstream Products

• 96854-34-1 (S)-3-phenyl-1,3-propanediol 
• 1426679-82-4 (1S,3R)-1-phenylhex-5-ene-1,3-diol 
• 1426679-83-5 (1S,3S)-1-phenylhex-5-ene-1,3-diol 
• 848900-98-1 (5S) ethyl δ-hydroxy-δ-phenyl-β-oxo-pentanoate 
• 146565-66-4 (S)-1-phenylpropane-1,3-diyl diacetate 

Relevant academic research and scientific papers

A flexible enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A using asymmetric transfer hydrogenation/tandem Grubbs cross-metathesis/oxy-Michael reaction as key steps

An efficient enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A was achieved by the use of asymmetric transfer hydrogenation (ATH)/tandem Grubbs cross-metathesis/oxy-Michael reaction. Furthermore, this strategy allows for diastereodiver

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.

Diastereo- and enantiomerically pure allylboronates: Their synthesis and scope

Allylboronates are highly attractive reagents for allyl additions. Enantiomerically pure, stable reagents with a stereogenic centre in a-position to boron are especially versatile, albeit often difficult to synthesize. Starting from boron-containing allyl alcohols 6 and 7, which are discussed in detail herein, a set of reagents were obtained via [3,3]-sigmatropic rearrangements and consecutive transformations in the side chain. The configurations could be established first by chemical correlation, but also by X-ray crystallography (16, 18, 34, and 39). Allyl additions were performed resulting in the formation of predominantly (Z)-configured homoallylic alcohols (31, 43-45) with high enantiomeric excess. Detailed investigations on the matched-mismatched interaction between the reagents 15/16 (and ent-15/ent-16, respectively) and isopropylidene glyceraldehyde 42 d are presented.

A concise total synthesis of diospongins A and B

The total synthesis of the diarylheptanoids (-)-diospongin A (1) and B (2) was achieved stereoselectively via the δ-lactone intermediate 6. The key reactions involved are a stereoselective reduction of β-keto ester and the Horner-Wadsworth-Emmons and intramolecular oxy-Michael reactions.

Remote asymmetric induction with vinylketene silyl N,O-acetal

A highly regio- and diastereoselective TiCl4-mediated vinylogous Mukaiyama aldol reaction using the chiral vinylketene silyl N,O-acetal has been developed. The present vinylogous Mukaiyama aldol reaction provides a unique and effective means of

Highly efficient enzymatic resolution of homoallyl alcohols leading to a simple synthesis of optically pure fluoxetine and related compounds

A practical method for enzymatic resolution of homoallyl alcohols and its utility in the synthesis of optically pure fluoxetine and related compounds is reported.

C-C ASYMMETRIC BOND FORMATION MEDIATED BY OPTICALLY ACTIVE SULFOXIDES

Highly stereoselective C-C bond forming reactions can be performed with a variety of optically active sulfinyl derivatives to afford, after desulfurization, optically active sulfur-free products.