Highly diastereoselective synthesis of enantioenriched: Anti -α-allyl-β-fluoroamines

Philip J. Chevis; Sirilak Wangngae; Thanaphat Thaima; Anthony W. Carroll; Anthony C. Willis; Mookda Pattarawarapan; Stephen G. Pyne

doi:10.1039/c9cc02765c

Highly diastereoselective synthesis of enantioenriched: Anti -α-allyl-β-fluoroamines

Philip J. Chevis, Sirilak Wangngae, Thanaphat Thaima, Anthony W. Carroll, Anthony C. Willis, Mookda Pattarawarapan, Stephen G. Pyne^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

A highly diastereoselective synthesis of anti-α-allyl-β-fluoroamines has been developed involving enantioselective α-fluorination of aldehydes followed by a diastereoselective Petasis allyl borono-Mannich reaction. The products are obtained generally in good overall yields for the two steps and with drs of 97:3-99:1 and ees of 86-92%. Selected products were converted to 3-, 5- and 6-membered ring heterocycles, the latter two types incorporating an exo-cyclic fluorine.

Original language	English
Pages (from-to)	6050-6053
Number of pages	4
Journal	Chemical Communications
Volume	55
Issue number	43
DOIs	https://doi.org/10.1039/c9cc02765c
Publication status	Published - 2019

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title = "Highly diastereoselective synthesis of enantioenriched: Anti -α-allyl-β-fluoroamines",

abstract = "A highly diastereoselective synthesis of anti-α-allyl-β-fluoroamines has been developed involving enantioselective α-fluorination of aldehydes followed by a diastereoselective Petasis allyl borono-Mannich reaction. The products are obtained generally in good overall yields for the two steps and with drs of 97:3-99:1 and ees of 86-92%. Selected products were converted to 3-, 5- and 6-membered ring heterocycles, the latter two types incorporating an exo-cyclic fluorine.",

author = "Chevis, {Philip J.} and Sirilak Wangngae and Thanaphat Thaima and Carroll, {Anthony W.} and Willis, {Anthony C.} and Mookda Pattarawarapan and Pyne, {Stephen G.}",

note = "Publisher Copyright: {\textcopyright} 2019 The Royal Society of Chemistry.",

year = "2019",

doi = "10.1039/c9cc02765c",

language = "English",

volume = "55",

pages = "6050--6053",

journal = "Chemical Communications",

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T1 - Highly diastereoselective synthesis of enantioenriched

T2 - Anti -α-allyl-β-fluoroamines

AU - Chevis, Philip J.

AU - Wangngae, Sirilak

AU - Thaima, Thanaphat

AU - Carroll, Anthony W.

AU - Willis, Anthony C.

AU - Pattarawarapan, Mookda

AU - Pyne, Stephen G.

PY - 2019

Y1 - 2019

N2 - A highly diastereoselective synthesis of anti-α-allyl-β-fluoroamines has been developed involving enantioselective α-fluorination of aldehydes followed by a diastereoselective Petasis allyl borono-Mannich reaction. The products are obtained generally in good overall yields for the two steps and with drs of 97:3-99:1 and ees of 86-92%. Selected products were converted to 3-, 5- and 6-membered ring heterocycles, the latter two types incorporating an exo-cyclic fluorine.

AB - A highly diastereoselective synthesis of anti-α-allyl-β-fluoroamines has been developed involving enantioselective α-fluorination of aldehydes followed by a diastereoselective Petasis allyl borono-Mannich reaction. The products are obtained generally in good overall yields for the two steps and with drs of 97:3-99:1 and ees of 86-92%. Selected products were converted to 3-, 5- and 6-membered ring heterocycles, the latter two types incorporating an exo-cyclic fluorine.

UR - http://www.scopus.com/inward/record.url?scp=85066149303&partnerID=8YFLogxK

U2 - 10.1039/c9cc02765c

DO - 10.1039/c9cc02765c

M3 - Article

SN - 1359-7345

VL - 55

SP - 6050

EP - 6053

JO - Chemical Communications

JF - Chemical Communications

IS - 43

ER -

Highly diastereoselective synthesis of enantioenriched: Anti -α-allyl-β-fluoroamines

Abstract

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