Lewis acid-activated chiral leaving group: enantioselective electrophilic addition to prochiral olefins.J Org Chem. 2002 Jul 26; 67(15):5124-37.JO
Abstract
A new strategy using a BINOL derivative as a chiral leaving group and Lewis acid has been developed for enantioselective alkylation of prochiral olefins. (R)-2,2'-Bis[2-(trimethylsilyl)ethoxymethyl]-1,1'-binaphthol is demonstrated to be an effective reagent for enantioselective hydroxymethylation of silyl enol ethers and trisubstituted alkenes. Electrophilic addition to prochiral olefins is accompanied by cleavage of an acetal that is dual activated by SnCl4 and the delta-effect of silicon through the S(N)2 substitution process. Enantioselective synthesis of cyclic terpenes is also described using this strategy.
Pub Type(s)
Journal Article
Language
eng
PubMed ID
12126396
Citation
Nakamura, Hiroko, et al. "Lewis Acid-activated Chiral Leaving Group: Enantioselective Electrophilic Addition to Prochiral Olefins." The Journal of Organic Chemistry, vol. 67, no. 15, 2002, pp. 5124-37.
Nakamura H, Ishihara K, Yamamoto H. Lewis acid-activated chiral leaving group: enantioselective electrophilic addition to prochiral olefins. J Org Chem. 2002;67(15):5124-37.
Nakamura, H., Ishihara, K., & Yamamoto, H. (2002). Lewis acid-activated chiral leaving group: enantioselective electrophilic addition to prochiral olefins. The Journal of Organic Chemistry, 67(15), 5124-37.
Nakamura H, Ishihara K, Yamamoto H. Lewis Acid-activated Chiral Leaving Group: Enantioselective Electrophilic Addition to Prochiral Olefins. J Org Chem. 2002 Jul 26;67(15):5124-37. PubMed PMID: 12126396.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Lewis acid-activated chiral leaving group: enantioselective electrophilic addition to prochiral olefins.
AU - Nakamura,Hiroko,
AU - Ishihara,Kazuaki,
AU - Yamamoto,Hisashi,
PY - 2002/7/20/pubmed
PY - 2002/7/20/medline
PY - 2002/7/20/entrez
SP - 5124
EP - 37
JF - The Journal of organic chemistry
JO - J Org Chem
VL - 67
IS - 15
N2 - A new strategy using a BINOL derivative as a chiral leaving group and Lewis acid has been developed for enantioselective alkylation of prochiral olefins. (R)-2,2'-Bis[2-(trimethylsilyl)ethoxymethyl]-1,1'-binaphthol is demonstrated to be an effective reagent for enantioselective hydroxymethylation of silyl enol ethers and trisubstituted alkenes. Electrophilic addition to prochiral olefins is accompanied by cleavage of an acetal that is dual activated by SnCl4 and the delta-effect of silicon through the S(N)2 substitution process. Enantioselective synthesis of cyclic terpenes is also described using this strategy.
SN - 0022-3263
UR - https://www.unboundmedicine.com/medline/citation/12126396/Lewis_acid_activated_chiral_leaving_group:_enantioselective_electrophilic_addition_to_prochiral_olefins_
DB - PRIME
DP - Unbound Medicine
ER -
