CAMPHOR-DERIVED 2-STANNYL-N-BOC-1,3-OXAZOLIDINE - A NEW CHIRAL FORMYLANION EQUIVALENT FOR THE ASYMMETRIC-SYNTHESIS OF 1,2-DIOLS

被引：51

作者：

COLOMBO, L

DIGIACOMO, M

BRUSOTTI, G

MILANO, E

机构：

[1] Dipartimento di Chimica Farmaceutica, Università di Pavia, I-27100 Pavia

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 16期

关键词：

D O I：

10.1016/0040-4039(95)00369-N

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically pure 2-tributylstannyl-N-Boc-1,3-oxazolidine 6, prepared from the camphor-derived aminoalcohol 5, was converted to diastereomerically pure 2-acyl derivatives 8 in three steps. Reaction of these ketones with Grignard reagents at -78 degrees C proceeded with high stereoselectivity affording tertiary carbinols which gave 1,2-diols with >96% ee after hydrolysis and reduction of the intermediate a-hydroxy aldehydes. A new deblocking procedure of the t-Boc group is also described.

引用

页码：2863 / 2866

页数：4

共 28 条

[1] ASYMMETRIC-SYNTHESIS OF HOMOCHIRAL 1,2-DIOLS VIA N-BOC OXAZOLIDINES
AGAMI, C
COUTY, F
LEQUESNE, C
TETRAHEDRON LETTERS, 1994, 35 (20) : 3309 - 3312
[2] CHIRAL GAMMA-(TETRAHYDROPYRANYLOXY)ALLYLSTANNANE - A NEW CHIRAL REAGENT FOR THE ASYMMETRIC-SYNTHESIS OF SYN 1,2-DIOLS
KADOTA, I
KOBAYASHI, K
OKANO, H
ASAO, N
YAMAMOTO, Y
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1995, 132 (5-6): : 615 - 623
[3] ASYMMETRIC-SYNTHESIS .4. PREPARATION OF CHIRAL ALPHA-AMINONITRILES FROM A NEW N-CYANOMETHYL-1,3-OXAZOLIDINE SYNTHON
MARCO, JL
ROYER, J
HUSSON, HP
TETRAHEDRON LETTERS, 1985, 26 (30) : 3567 - 3570
[4] ASYMMETRIC-SYNTHESIS OF SYN 1,2-DIOLS VIA THE REACTION OF ALDEHYDES WITH CHIRAL GAMMA-(TETRAHYDROPYRANYLOXY)ALLYLSTANNANES
YAMAMOTO, Y
KOBAYASHI, K
OKANO, H
KADOTA, I
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26): : 7003 - 7005
[5] Asymmetric synthesis of new chiral 1,2- and 1,3-diols
Tülay Yıldız
Ayşe Yusufoğlu
Monatshefte für Chemie - Chemical Monthly, 2013, 144 : 183 - 190
[6] Asymmetric synthesis of new chiral 1,2-and 1,3-diols
Yildiz, Tulay
Yusufoglu, Ayse
MONATSHEFTE FUR CHEMIE, 2013, 144 (02): : 183 - 190
[7] ASYMMETRIC-SYNTHESIS MONITORED BY CHIRAL SULFOXIDES - SYN AND ANTI FUNCTIONALIZED 1,2-DIOLS FROM ALPHA-HYDROXY-ESTERS
SOLLADIE, G
ALMARIO, A
TETRAHEDRON LETTERS, 1994, 35 (12) : 1937 - 1940
[8] Asymmetric synthesis of (+)- and (-)-dihydropinidines:: diastereoselective addition to chiral imine or 1,3-oxazolidine derived from (R)-phenylglycinol as a single starting material with organometallic reagents
Yamauchi, T
Fujikura, H
Higashiyama, K
Takahashi, H
Ohmiya, S
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (19): : 2791 - 2794
[9] Design and synthesis of novel C2-symmetric chiral piperazines and an application to asymmetric acylation of σ-symmetric 1,2-diols
Nakamura, Daisuke
Kakiuchi, Kiyomi
Koga, Kenji
Shirai, Ryuichi
ORGANIC LETTERS, 2006, 8 (26) : 6139 - 6142
[10] Dispiroketals in Synthesis (Part 21)1: Use of Chiral 2,2'-Bis(halomethyl)dihydropyrans as New Protecting and Resolving Agents for 1,2-Diols
Synlett, 8 (789):

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