Stereoselective Allylation of Linear and Chiral β-Amino-α-Hydroxy Aldehydes: Total Syntheses of Tetraacetyl d-lyxo-, d-ribo-, and 
d-arabino-Phytosphingosines

In-Soo Myeong; Jin-Seok Kim; Muyng-Gyu Park; Hwan-Hee Jeon; Changyoung Jung; Yong-Taek Lee; Won-Hun Ham

doi:10.1055/s-0037-1609343

Synthesis, Table of Contents

Synthesis 2018; 50(10): 2058-2066
DOI: 10.1055/s-0037-1609343

paper

Stereoselective Allylation of Linear and Chiral β-Amino-α-Hydroxy Aldehydes: Total Syntheses of Tetraacetyl d-lyxo-, d-ribo-, and d-arabino-Phytosphingosines

In-Soo Myeong

School of Pharmacy, Sungkyunkwan University, Seobu-ro 2066, Suwon-si, Gyeonggi-do 16419, Republic of Korea Email: whham@skku.edu

,

Jin-Seok Kim

School of Pharmacy, Sungkyunkwan University, Seobu-ro 2066, Suwon-si, Gyeonggi-do 16419, Republic of Korea Email: whham@skku.edu

,

Muyng-Gyu Park

School of Pharmacy, Sungkyunkwan University, Seobu-ro 2066, Suwon-si, Gyeonggi-do 16419, Republic of Korea Email: whham@skku.edu

,

Hwan-Hee Jeon

School of Pharmacy, Sungkyunkwan University, Seobu-ro 2066, Suwon-si, Gyeonggi-do 16419, Republic of Korea Email: whham@skku.edu

,

Changyoung Jung

School of Pharmacy, Sungkyunkwan University, Seobu-ro 2066, Suwon-si, Gyeonggi-do 16419, Republic of Korea Email: whham@skku.edu

,

Yong-Taek Lee

School of Pharmacy, Sungkyunkwan University, Seobu-ro 2066, Suwon-si, Gyeonggi-do 16419, Republic of Korea Email: whham@skku.edu

,

Won-Hun Ham*

School of Pharmacy, Sungkyunkwan University, Seobu-ro 2066, Suwon-si, Gyeonggi-do 16419, Republic of Korea Email: whham@skku.edu

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Abstract

The stereoselective allylations of β-amino-α-hydroxy aldehydes are described. Several Lewis acids (BF₃·OEt₂, SnCl₄, TiCl₄, ZnCl₂, and MgBr₂·OEt₂) were utilized in the allylations. The allylation of anti-β-NHCbz-α-OTBS substrate mediated by SnCl₄ afforded the syn-selective product, while its allylation mediated by BF₃·OEt₂ afforded the anti-selective product. The allylation of syn-β-NHCbz-α-OTBS mediated by SnCl₄ afforded the anti-selective product. The mechanism involves the chelation between the amido group and aldehyde oxygen by SnCl₄, and the Felkin–Anh model by BF₃·OEt₂. The resulting allylation products were used for the total syntheses of tetraacetyl d-lyxo-, d-ribo-, and d-arabino-phytosphingosines.

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