Desymmetrization of 4-dimethylsiloxy-1,6-heptadiynes through sequential double silylformylation

Dominique Bonafoux; Iwao Ojima

doi:10.1021/ol0156594

Desymmetrization of 4-dimethylsiloxy-1,6-heptadiynes through sequential double silylformylation

Dominique Bonafoux
, Iwao Ojima

Chemistry

Stony Brook University

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

16 Scopus citations

Abstract

(equation presented) Desymmetrization of dimethylsilyloxyalkadiynes (1) by Rh-catalyzed intramolecular silylformylation affords 5-exo-(formylmethylene)-oxasilacyclopentanes 2 in high yields. Novel sequential double silylformylation of 1a also provides desymmetrization, giving 3-(3-silyl-2-formylprop-2-enyl)-5-exo-(formylmethylene)oxasilacyclopentanes 4 in excellent yields. Reduction of 2a and 4 with NaBH₄ gives the corresponding 5-exo(hydroxymethylmethylene)oxasilacyclopentanes 3a and 5, respectively.

Original language	English
Pages (from-to)	1303-1304
Number of pages	2
Journal	Organic Letters
Volume	3
Issue number	9
DOIs	https://doi.org/10.1021/ol0156594
State	Published - May 3 2001

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title = "Desymmetrization of 4-dimethylsiloxy-1,6-heptadiynes through sequential double silylformylation",

abstract = "(equation presented) Desymmetrization of dimethylsilyloxyalkadiynes (1) by Rh-catalyzed intramolecular silylformylation affords 5-exo-(formylmethylene)-oxasilacyclopentanes 2 in high yields. Novel sequential double silylformylation of 1a also provides desymmetrization, giving 3-(3-silyl-2-formylprop-2-enyl)-5-exo-(formylmethylene)oxasilacyclopentanes 4 in excellent yields. Reduction of 2a and 4 with NaBH4 gives the corresponding 5-exo(hydroxymethylmethylene)oxasilacyclopentanes 3a and 5, respectively.",

author = "Dominique Bonafoux and Iwao Ojima",

year = "2001",

month = may,

day = "3",

doi = "10.1021/ol0156594",

language = "English",

volume = "3",

pages = "1303--1304",

journal = "Organic Letters",

issn = "1523-7060",

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T1 - Desymmetrization of 4-dimethylsiloxy-1,6-heptadiynes through sequential double silylformylation

AU - Bonafoux, Dominique

AU - Ojima, Iwao

PY - 2001/5/3

Y1 - 2001/5/3

N2 - (equation presented) Desymmetrization of dimethylsilyloxyalkadiynes (1) by Rh-catalyzed intramolecular silylformylation affords 5-exo-(formylmethylene)-oxasilacyclopentanes 2 in high yields. Novel sequential double silylformylation of 1a also provides desymmetrization, giving 3-(3-silyl-2-formylprop-2-enyl)-5-exo-(formylmethylene)oxasilacyclopentanes 4 in excellent yields. Reduction of 2a and 4 with NaBH4 gives the corresponding 5-exo(hydroxymethylmethylene)oxasilacyclopentanes 3a and 5, respectively.

AB - (equation presented) Desymmetrization of dimethylsilyloxyalkadiynes (1) by Rh-catalyzed intramolecular silylformylation affords 5-exo-(formylmethylene)-oxasilacyclopentanes 2 in high yields. Novel sequential double silylformylation of 1a also provides desymmetrization, giving 3-(3-silyl-2-formylprop-2-enyl)-5-exo-(formylmethylene)oxasilacyclopentanes 4 in excellent yields. Reduction of 2a and 4 with NaBH4 gives the corresponding 5-exo(hydroxymethylmethylene)oxasilacyclopentanes 3a and 5, respectively.

UR - https://www.scopus.com/pages/publications/0035799852

U2 - 10.1021/ol0156594

DO - 10.1021/ol0156594

M3 - Article

C2 - 11348220

AN - SCOPUS:0035799852

SN - 1523-7060

VL - 3

SP - 1303

EP - 1304

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Desymmetrization of 4-dimethylsiloxy-1,6-heptadiynes through sequential double silylformylation

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