Intramolecular Sakurai Allylation of Geminal Bis(silyl) Enamide with Indolenine. A Diastereoselective Cyclization To Form Functionalized Hexahydropyrido[3,4-b]Indole
Publication type: Journal Article
Publication date: 2020-12-21
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
33346667
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A fluoride-promoted intramolecular Sakurai allylation of geminal bis(silyl) enamide with indolenine has been developed. The reaction facilitates an efficient cyclization to give hexahydropyrido[3,4-b]indoles in good yields with high diastereoselectivity. The resulted cis, trans-stereochemistry further enables the ring-closing metathesis (RCM) reaction of two alkene moieties, giving a tetracyclic N-hetereocycle widely found as the core structure in akuammiline alkaloids.
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Total citations:
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Citations from 2024:
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(14.29%)
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Chen Y. et al. Intramolecular Sakurai Allylation of Geminal Bis(silyl) Enamide with Indolenine. A Diastereoselective Cyclization To Form Functionalized Hexahydropyrido[3,4-b]Indole // Organic Letters. 2020. Vol. 23. No. 1. pp. 124-128.
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Chen Y., Song X., Gao L., Song Z. Intramolecular Sakurai Allylation of Geminal Bis(silyl) Enamide with Indolenine. A Diastereoselective Cyclization To Form Functionalized Hexahydropyrido[3,4-b]Indole // Organic Letters. 2020. Vol. 23. No. 1. pp. 124-128.
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TY - JOUR
DO - 10.1021/acs.orglett.0c03806
UR - https://doi.org/10.1021/acs.orglett.0c03806
TI - Intramolecular Sakurai Allylation of Geminal Bis(silyl) Enamide with Indolenine. A Diastereoselective Cyclization To Form Functionalized Hexahydropyrido[3,4-b]Indole
T2 - Organic Letters
AU - Chen, Yi
AU - Song, Xuanyi
AU - Gao, Lu
AU - Song, Zhenlei
PY - 2020
DA - 2020/12/21
PB - American Chemical Society (ACS)
SP - 124-128
IS - 1
VL - 23
PMID - 33346667
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2020_Chen,
author = {Yi Chen and Xuanyi Song and Lu Gao and Zhenlei Song},
title = {Intramolecular Sakurai Allylation of Geminal Bis(silyl) Enamide with Indolenine. A Diastereoselective Cyclization To Form Functionalized Hexahydropyrido[3,4-b]Indole},
journal = {Organic Letters},
year = {2020},
volume = {23},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/acs.orglett.0c03806},
number = {1},
pages = {124--128},
doi = {10.1021/acs.orglett.0c03806}
}
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MLA
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Chen, Yi, et al. “Intramolecular Sakurai Allylation of Geminal Bis(silyl) Enamide with Indolenine. A Diastereoselective Cyclization To Form Functionalized Hexahydropyrido[3,4-b]Indole.” Organic Letters, vol. 23, no. 1, Dec. 2020, pp. 124-128. https://doi.org/10.1021/acs.orglett.0c03806.