2406-16-8

Upstream product

• 88314-79-8 (R)-5-methyl-5-phenyl-3,4-dihydro(5H)-furan-2-one 

Downstream Products

• 345306-06-1 Acetic acid (R)-4-hydroxy-4-phenyl-pentyl ester 
• 345306-09-4 toluene-4-sulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-4-phenyl-pentyl ester 
• 345306-07-2 acetic acid 4-(tert-butyl-dimethyl-silanyloxy)-4-phenyl-pentyl ester 
• 345306-11-8 tert-butyl-dimethyl-(1-methyl-1-phenyl-hexyloxy)-silane 
• 345306-08-3 4-(tert-butyl-dimethyl-silanyloxy)-4-phenyl-pentan-1-ol 
• 345306-10-7 tert-butyl-dimethyl-(1-methyl-1-phenyl-pentyloxy)-silane 
• 73464-88-7 (R)-2-phenyl-hexan-2-ol 

Relevant academic research and scientific papers

Borabicyclo[3.3.2]decanes and the stereoselective asymmetric synthesis of 1,3-diol stereotriads from 1,3-diborylpropenes

The synthesis of mixed borabicyclodecane (BBD)-derived 1,3-diborylpropenes (trans-1)is described. These new bimetallic reagents are effective for the selective asymmetric allylboration first of ketones (or ketimines)and second of aldehydes (or aldimines). Formed as a thermodynamic mixtu re of trans regioisomers from cis-1 through a series of 1,3-borotropic shifts, only trans-1 undergoes the monoallylation of ketones. After this single addition, this process is effectively shut down after the reaction of the 10-Ph-9-BBD portion in 1. Serving as a molecular gate, the rearranged 10-TMS-9-BBD trans allylborane intermediate 11 reacts only after an aldehyde (or aldimine) is added. This allylation fixes the last two stereogenic centers of the 2-vinyl-1,3-diol stereotriad, ultimately resulting in 16 (or 1,3-amino alcohols) in 50-72percent yield (>98percent ee)as single observable diastereomers. These reagents 1 uniquely function as the equivalent of 1,1-bimetallic allylic reagents, adding sequentiall y first to ketones and second to aldehydes.

Efficient 1,8- and 1,9-asymmetric inductions in the Grignard reaction of δ- and ε-keto esters of 1,1′-binaphthalen-2-ols with an oligoether tether as the 2′-substituent: Application to the synthesis of (-)-malyngolide

Efficient 1,8- and 1,9-asymmetric inductions in the Grignard reaction of podand-type δ- (3,4) and ε-keto esters (5,6) are achieved in the presence of MgBr2·OEt2 with up to 97 and 82% optical yields, respectively, by using 2′-[3-(2-methoxyethoxy)propoxy]-1,1′-binaphthalen-2-ol as the chiral auxiliary. The 1,8-asymmetric inductive Grignard reaction has been advantageously utilized in the key step of a synthesis of (-)-malyngolide.