883884-89-7

Upstream product

• 1178609-37-4 C₃₄H₃₅BO₇S 
• 557-20-0 diethylzinc 
• 1044871-05-7 (4'R,5'R,1E)-1-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]-3-chloro-2-propene 
• 130874-89-4 (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butandiol 
• 652993-64-1 (3S,4'R,5'R)-ethyl 3-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]pent-4-enoate 
• 883884-85-3 (3S,4'R,5'R)-3-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]pent-4-en-1-ol 
• 883884-87-5 (3S,4'R,5'R)-3-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]pent-4-en-1-yl methanesulfonate 

Downstream Products

• 1044871-72-8 (2S,4Z)-1-(4'-methoxybenzyloxy)hept-4-en-2-ol 
• 1044871-69-3 (3R,5Z)-1-phenyloct-5-en-3-ol 

Relevant academic research and scientific papers

Enantioselective Catalysts for the Synthesis of α-Substituted Allylboronates - An Accelerated Approach towards Isomerically Pure Homoallylic Alcohols

The use of a convenient protecting group for boronates allows a selective, catalyzed SN2′ reaction to generate allylboronates which are applied for the synthesis of enantiomerically pure homoallylic alcohols. Depending on the configuration of both catalyst and the protecting group any of the four possible stereoisomers can be formed. The rationale behind the selective addition is supported by density functional theory calculations.

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.

New enantiomerically pure allylboronic esters in allyl additions: Synthesis and NMR investigation of intermediates

Enantiomerically pure allylboronic esters 1 + 2 with a stereogenic center α to the boron moiety can be obtained by a sigmatropic rearrangement of boron containing allyl alcohols. Allyl additions with the new reagents are highly selective, which was shown